Benzyl Chloride → (S)-4-benzyloxy-1-trityloxy-2-butanol

HRID 1168058Notes

Reaction equation

HRID 1168058 reaction equation
[H-].[Na+].CCCCCC.[C:9]([O:28][CH2:29][C@@H:30]([OH:34])[CH2:31][CH2:32][OH:33])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:35](Cl)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CS(C)=O.O>[CH2:35]([O:33][CH2:32][CH2:31][C@H:30]([OH:34])[CH2:29][O:28][C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 8058HexaneHCID 24758Sodium hydrideHCID 14027585(S)-1-trityloxy-2,4-butanediol

Product 1

HCID 11015650(S)-4-benzyloxy-1-trityloxy-2-butanolYield 45%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Sodium hydride (74 mg, 1.85 mmol, 60% in oil) was loaded under argon circumstance in three necked flask and hexane (2 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) (2 ml) was added and the solution was cooled to 0° C. (S)-1-Trityloxy-2,4-butandiol (0.62 g, 1.68 mmol) prepared by Example 2-(2) in DMSO (3 ml) was dropped by taking care of the temperature over a one hour period at room temperature to the solution. Then the solution was stirred for 1 hour. To the solution was dropped benzyl chloride (0.213 ml, 1.85 mol) in DMSO (3 ml) over a one hour period at the range of 0° C. to 5° C. and then the solution was stirred for 4 hours. To the reaction mixture was added water (5 ml) and the solution was extracted with ethyl acetate. The extract was washed with water (8 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 (S)-4-benzyloxy-1-trityloxy-2-butanol (0.32 g, yield 45%).

Workup

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

Sources & evidence

ORD record
ord-e356462225e444a9ab3138291f7190d8
Source dataset
uspto-grants-2003_09
Patent number
US06620977B1

Reaction notes

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