Water → HCID 22799884, compound

HRID 973349Notes

Reaction equation

HRID 973349 reaction equation
[OH:1][C@@H:2]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:3][CH2:4][CH2:5][C:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:37](OC(=O)C)(=[O:39])[CH3:38].O>N1C=CC=CC=1.CCOCC>[C:10]([O:9][C:7](=[O:8])[C:6]([CH2:5][CH2:4][CH2:3][C@@H:2]([O:1][C:37](=[O:39])[CH3:38])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:12])([CH3:13])[CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22799885HCID 22799885, compound

Product 1

HCID 22799884HCID 22799884, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Di-tert.-butyl 2-[4-(S)-hydroxynonyl]-2-(6-ethoxycarbonylhexyl)malonate (39.0 g., 0.076 mole) is dissolved in pyridine (50 ml.). Acetic anhydride (8.2 g., 0.08 mole) is added dropwise during 15 minutes and the mixture is stirred and heated at 60° C. for 3 hours. The mixture is then cooled and treated with 300 ml. water. The oily product is taken up in ether, washed with 5% hydrochloric acid, two portions of water and brine, and dried over sodium sulfate. Distillation of the ether in vacuo leaves the title compound as a residual oil weighing 41 g.

Workup

  1. temperatureThe mixture is then cooled
  2. additiontreated with 300 ml
  3. washwashed with 5% hydrochloric acid, two portions of water and brine
  4. dry with materialdried over sodium sulfate
  5. distillationDistillation of the ether in vacuo

Sources & evidence

ORD record
ord-5186f1eb36c94c7b92aa05f0705a43ef
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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