Pyridine → (rac)-1-O-dodecyl-2-O-methoxycarbonyl-3-O-trityl-glycerol

HRID 2412546Notes

Reaction equation

HRID 2412546 reaction equation
[CH2:1]([O:13][CH2:14][CH:15]([CH2:17][O:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].N1C=CC=CC=1.Cl[C:45]([O:47][CH3:48])=[O:46]>C(Cl)Cl>[CH2:1]([O:13][CH2:14][CH:15]([CH2:17][O:18][C:19]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[O:16][C:45]([O:47][CH3:48])=[O:46])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 159268043-Dodecyloxy-1-triphenylmethoxy-2-propanol

Product 1

HCID 54191648(rac)-1-O-dodecyl-2-O-methoxycarbonyl-3-O-trityl-glycerolYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (rac)-1-O-dodecyl-3-O-trityl-glycerol (16.0 g) and dry pyridine (7.54 g) in dry methylenechloride (200 ml) was added, dropwise over 20 minutes, a solution of methyl chloroformate (5.70 g) in dry methylene chloride (40 ml) at 5° C. After 3 hours, the solution was allowed to stand for 17 hours at ambient temperature, and then washed with aqueous hydrochloric acid and water, dried, and evaporated. The residue was purified by column chromatography on silica gel (240 g, elution by chloroform) to yield 17.33 g of (rac)-1-O-dodecyl-2-O-methoxycarbonyl-3-O-trityl-glycerol as a colorless oil.

Workup

  1. customat 5° C
  2. waitto stand for 17 hours at ambient temperature
  3. washwashed with aqueous hydrochloric acid and water
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (240 g, elution by chloroform)

Sources & evidence

ORD record
ord-984fb184651a46809beff58be8335684
Source dataset
uspto-grants-1985_01
Patent number
US04493832

Reaction notes

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