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Hexane → (S)-4-benzyloxy-2-(2-benzyloxyethoxy)-1-trityloxybutane

HRID 1168050
Notes
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Reaction equation

HRID 1168050 reaction equation
[H-].[Na+].CCCCCC.[CH2:9]([O:16][CH2:17][CH2:18][C@H:19]([OH:41])[CH2:20][O:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CS(O[CH2:47][CH2:48][O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=O)=O>CS(C)=O.O>[CH2:9]([O:16][CH2:17][CH2:18][C@H:19]([O:41][CH2:47][CH2:48][O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:20][O:21][C:22]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 108572722-Benzyloxyethyl mesylateHCID 11015650(S)-4-benzyloxy-1-trityloxy-2-butanol

Product 1

HCID 10907940(S)-4-benzyloxy-2-(2-benzyloxyethoxy)-1-trityloxybutaneYield 75%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
2×
HCID 962WaterSolvent

Procedure

Sodium hydride (6.32 g, 0.158 mmol, 60% in oil) was loaded under argon circumstance in three-necked flask and hexane (100 ml) was added thereto. After stirring for a while, it was allowed to stand and the supernatant was removed by syringe. By repeating this procedure three times, the oil of sodium hydride was removed. After drying in vacuo anhydrous dimethyl sulfoxide (DMSO) (30 ml) was added and the solution was stirred at 60° C. for 1 hour. After cooling to room temperature, (S)-4-benzyloxy-1-trityloxy-2-butanol (55.89 g, 0.132 mol) in DMSO (40 ml) was gradually dropped at room temperature to the solution and then the solution was stirred for 30 minutes. To the solution was gradually dropped 2-benzyloxyethyl methanesulfonate (33.4 g, 0.145 mol) in DMSO (40 ml) at room temperature and then the solution was stirred for 12 hours. To the reaction mixture was added water (120 ml) and the solution was extracted with ethyl acetate. The extract was washed with water (150 ml) twice and with saturated brine once, dried on sodium sulfate, filtered and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-4-benzyloxy-2-(2-benzyloxyethoxy)-1-trityloxybutane (55.0 g, yield 75%).

Workup

  1. customthe supernatant was removed by syringe
  2. customthe oil of sodium hydride was removed
  3. dry with materialAfter drying in vacuo anhydrous dimethyl sulfoxide (DMSO) (30 ml)
  4. additionwas added
  5. stirringthe solution was stirred at 60° C. for 1 hour
  6. stirringthe solution was stirred for 30 minutes
  7. customat room temperature
  8. stirringthe solution was stirred for 12 hours
  9. extractionthe solution was extracted with ethyl acetate
  10. washThe extract was washed with water (150 ml) twice
  11. dry with materialwith saturated brine once, dried on sodium sulfate
  12. filtrationfiltered
  13. customcondensed in vacuo

Sources & evidence

ORD record
ord-9da972368d6d49d9a6e1b15a99ab6fd0
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06620977B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes