Methanol → HCID 11729567, compound

HRID 1692187Notes

Reaction equation

HRID 1692187 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:28][CH2:29][C@@H:30]([CH2:32][OH:33])[OH:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)C1C=CN=CC=1)C.CO>N1C=CC=CC=1>[CH2:21]([O:28][CH2:29][C@H:30]([CH2:32][O:33][C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6456Trityl chlorideHCID 2724795(R)-3-(benzyloxy)propane-1,2-diolHCID 117687514-Diethylaminopyridine

Product 1

HCID 11729567HCID 11729567, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trityl chloride (56 g) was added portionswise to a solution of 1-O-benzyl-(R)-glycerol (36.4 g, 0.2 mol) and 4-diethylaminopyridine (1 g) in pyridine (300 mL) under stirring and cooling with ice. After 20 h stirring methanol (50 mL) was added, the mixture was stirred for 30 min and concentrated in vacuo to half of the original volume. Ethyl acetate (500 mL) was added and the mixture extracted with water (3×250 mL). The organic layer was briefly dried with MgSO4, filtered and evaporated in vacuo. The residue 4 was codistilled with toluene (200 ml portions) to remove the residual pyridine and used for further synthesis.

Workup

  1. temperaturecooling with ice
  2. additionwas added
  3. stirringthe mixture was stirred for 30 min
  4. concentrationconcentrated in vacuo to half of the original volume
  5. additionEthyl acetate (500 mL) was added
  6. extractionthe mixture extracted with water (3×250 mL)
  7. dry with materialThe organic layer was briefly dried with MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto remove the residual pyridine
  11. customused for further synthesis

Sources & evidence

ORD record
ord-38e4ae3d2983481fbd9065eb37b017cf
Source dataset
uspto-grants-2012_04
Patent number
US08153787B2

Reaction notes

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