Trichloroethylene → HCID 86738644, compound

HRID 2199014Notes

Reaction equation

HRID 2199014 reaction equation
[C:1]([CH:18]([OH:46])[C@H:19]([C@H:21]([C@@H:23]([C@@H:25]([CH:27]([C:29](=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[OH:28])[OH:26])[OH:24])[OH:22])[OH:20])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl[CH:48]=[C:49](Cl)Cl>N1C=CC=CC=1>[C:1]([CH:18]([OH:46])[C@:19]([C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:48][CH3:49])([C@H:21]([C@@H:23]([C@@:25]([C:19](=[O:20])[CH2:21][CH2:23][CH2:25][CH2:27][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])([CH:27]([C:29](=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[OH:28])[OH:26])[OH:24])[OH:22])[OH:20])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 6575TrichloroethyleneHCID 86738645HCID 86738645, compound

Product 1

HCID 86738644HCID 86738644, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-18 °C

Procedure

3.3 g of 1,6-dipalmitoyl-D-mannitol and 0.53 of benzene boronic acid anhydride was added to a solution containing 20 ml of pyridine and 20 ml of trichloroethylene, and the mixture was dried with 5 g of molecular sieves. The mixture was cooled at -18° C. and 3.3 g of oleoyl chloride, dissolved in 10 ml of trichloroethylene, was added. The mixture was left standing over night at -18° C. and for four hours at room temperature. The reaction mixture was washed with 120 ml of 2 N hydrochloric acid and with water, and fractionated in a column containing 160 g of Sephadex LH 20 and eluting with a 1:1-mixture of chloroform and ethanol (90%), whereby the boronic acid protection was removed.

Workup

  1. customthe mixture was dried with 5 g of molecular sieves
  2. dissolution3.3 g of oleoyl chloride, dissolved in 10 ml of trichloroethylene
  3. additionwas added
  4. waitThe mixture was left
  5. washThe reaction mixture was washed with 120 ml of 2 N hydrochloric acid and with water
  6. additioncontaining 160 g of Sephadex LH 20
  7. washeluting with a 1
  8. custom1-mixture of chloroform and ethanol (90%), whereby the boronic acid protection was removed

Sources & evidence

ORD record
ord-6d72e4e5176046ba99170cf11857195d
Source dataset
uspto-grants-1982_11
Patent number
US04360694

Reaction notes

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