Pyridine → 1-o-t-Butyldimethylsilyl-2-o-methyl-3-o-oleoyl-rac-glycerol

HRID 854715Notes

Reaction equation

HRID 854715 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([CH2:13][OH:14])[O:11][CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15](Cl)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].N1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[O:11][CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5364783Oleoyl chlorideHCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

Product 1

HCID 877595431-o-t-Butyldimethylsilyl-2-o-methyl-3-o-oleoyl-rac-glycerolYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol Compound 42 (1.1 g, 5.0 mmol) in CH2Cl2 (10 mL) was added oleoyl chloride (1.8 mL, 5.5 mmol) followed, after 5 min, by the addition of pyridine (0.44 mL, 5.5 mmol). After TLC analysis indicated that the reaction had gone to completion, the mixture was partitioned between ethyl acetate (100 mL) and H2O (30 mL), the organic extract was dried (MgSO4) and concentrated to give 1-O-t-butyldimethylsilyl-2-O-methyl-3-O-oleoyl-rac-glycerol (Compound 43) (2.4 g, 99%) as a dark brown oil.

Workup

  1. customthe mixture was partitioned between ethyl acetate (100 mL) and H2O (30 mL)
  2. extractionthe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67efcb0fb39d481b81787486c034cacc
Source dataset
uspto-grants-2007_08
Patent number
US07259273B1

Reaction notes

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