Hydrochloric Acid → HCID 18612291, compound

HRID 2082175Notes

Reaction equation

HRID 2082175 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-02869cb6b265410db52a0f321d48ca77
Source dataset
uspto-grants-1993_02
Patent number
US05187293

Reaction notes

Loading…