Triethylamine → HCID 18612293, compound

HRID 2082171Notes

Reaction equation

HRID 2082171 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.C(N(CC)CC)C.[Cl:39][CH2:40][CH2:41][CH2:42][C:43](Cl)=[O:44]>C(Cl)(Cl)Cl>[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:43](=[O:44])[CH2:42][CH2:41][CH2:40][Cl:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 115538421-Propanol, 3-(octadecyloxy)-2-(phenylmethoxy)-, (S)-

Product 1

HCID 18612293HCID 18612293, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A solution of 0.5 g of (S)-2-O-benzyl-1-O-octadecylglycerine and 0.16 ml of triethylamine in 2 ml of chloroform is added dropwise to a solution, cooled to 0° C., of 0.16 ml of 4-chlorobutyryl chloride in 1 ml of chloroform. The reaction mixture is stirred at room temperature, diluted with 5 ml of chloroform and washed in succession with 5 ml of 1N sodium hydroxide and 3×10 ml of water. The organic phase is dried and concentrated. The residue is chromatographed on silica gel while eluting with hexane-ether (19:1). There is obtained (R)-2-O-benzyl-1-O-(4-chlorobutyryl)-3-O-octadecylglycerine in the form of an oily residue.

Workup

  1. washwashed in succession with 5 ml of 1N sodium hydroxide and 3×10 ml of water
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel
  5. washwhile eluting with hexane-ether (19:1)

Sources & evidence

ORD record
ord-b55a5c4630264692b6b47da3be019147
Source dataset
uspto-grants-1993_02
Patent number
US05187293

Reaction notes

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