Hydrochloric Acid → HCID 13356685, compound

HRID 1587146Notes

Reaction equation

HRID 1587146 reaction equation
C[C@@H]([C@@H]1[C@@]2(C)CCC3[C@@]4(C)CCC(OC([Cl:29])=O)CC4=CCC3C2CC1)CCCC(C)C.[CH2:32]([O:39][CH:40]([CH2:43][OH:44])[CH2:41]O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>C(Cl)Cl.N1C=CC=CC=1.O>[CH2:32]([O:39][CH:40]([CH2:43][OH:44])[CH2:41][Cl:29])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 2035672-(Phenylmethoxy)-1,3-propanediolHCID 54236888C28H45ClO2

Product 1

HCID 13356685HCID 13356685, compoundYield 135.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.2 g of cholesteryl chloroformate in 130 ml of methylene chloride is treated under argon while stirring with 4.6 g of 2-O-benzylglycerol in 120 ml of methylene chloride and 2 ml of pyridine, taken up in 500 ml of water and 50 ml of 1N HCl after 1 hour and extracted with methylene chloride. The organic phase is dried and concentrated at 50° C. After chromatography over SiO2 with n-hexane:ether (1:1) there are obtained 6.17 g of (RS)-2-(benzyloxy)-3-hydroxypropyl chloride 5-en-3β-ylcarbonate, MS: 595 (M+H+), the starting material of Example 13.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase is dried
  3. concentrationconcentrated at 50° C

Sources & evidence

ORD record
ord-ce5ce4d06a3f45f192941d8a50e85cf5
Source dataset
uspto-grants-1993_06
Patent number
US05215972

Reaction notes

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