Hydrochloric Acid → HCID 18612291, compound

HRID 569130Notes

Reaction equation

HRID 569130 reaction equation
[CH2:1]([O:8][C@@H:9]([CH2:30][OH:31])[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:39]([O:41][CH2:42][CH2:43][Br:44])=[O:40].Cl>ClCCl.O>[CH2:1]([O:8][C@H:9]([CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:30][O:31][C:39]([O:41][CH2:42][CH2:43][Br:44])=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 785282-Bromoethyl chloroformateHCID 115538421-Propanol, 3-(octadecyloxy)-2-(phenylmethoxy)-, (S)-

Product 1

HCID 18612291HCID 18612291, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.5 g of (S)-2-O-benzyl-1-O-octadecyl glycerine in 25 ml of dichloromethane is treated with 0.3 ml of pyridine and cooled to 0° C. The solution is treated with 0.2 ml of 2-bromoethyl chloroformate, stirred at room temperature, treated with 10 ml of water and acidified to pH 3 with 1N hydrochloric acid. The organic phase is washed with water, dried and evaporated. The residue is chromatographed on silica gel while eluting with ether/n-hexane (1:1). There is obtained (R)-2-O-benzyl-1-[(2-bromoethoxy)carbonyl]-3-O-octadecylglycerine in the form of an oil.

Workup

  1. washThe organic phase is washed with water
  2. customdried
  3. customevaporated
  4. customThe residue is chromatographed on silica gel
  5. washwhile eluting with ether/n-hexane (1:1)

Sources & evidence

ORD record
ord-f2bf6c8b524140c699f61fd5ca24e9f0
Source dataset
uspto-grants-1988_03
Patent number
US04731373

Reaction notes

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