Water → HCID 20075597, compound

HRID 704139Notes

Reaction equation

HRID 704139 reaction equation
[CH2:1]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:2]([CH3:4])[CH3:3].[H-].[Na+].Cl[CH2:19][S:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C1(C)C=CC=CC=1>[CH2:21]([S:20][CH2:19][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 25047Diethyl isobutylmalonateHCID 319930Benzyl Chloromethyl Sulfide

Product 1

HCID 20075597HCID 20075597, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Diethyl isobutylmalonate (22.0 g.) was added to a stirred suspension of sodium hydride (4.8 g. 50% dispersion in oil) in dry toluene (200 ml.), under nitrogen. The mixture was stirred at 80° for one hour. The mixture was cooled and benzyl chloromethyl thioether 5 (16.0 g.) in dry toluene (50 ml.) was added and the mixture was stirred at 80° for two hours. The mixture was cooled and poured into water. The aqueous mixture was extracted into diethyl ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. Diethyl 2-benzylthiomethyl-2-isobutylmalonate (32.0 g.) was obtained as a yellow oil and was used without further purification.

Workup

  1. temperatureThe mixture was cooled
  2. stirringthe mixture was stirred at 80° for two hours
  3. temperatureThe mixture was cooled
  4. extractionThe aqueous mixture was extracted into diethyl ether
  5. washThe ether extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-439d5bfe21af4a6582326cacfb56f26a
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

Loading…