Sodium hydride → HCID 22990238, compound

HRID 981804Notes

Reaction equation

HRID 981804 reaction equation
[H-].[Na+].C(OP(OCC)([C:8]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][C:9]=1[CH3:19])=O)C.[C:23]([C:26]1[CH:27]=[CH:28][C:29]2[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[CH2:32][CH2:31][C:30]=2[CH:38]=1)(=O)[CH3:24]>CN(C)C=O>[CH3:36][C:33]1([CH3:37])[CH2:32][CH2:31][C:30]2[CH:38]=[C:26](/[C:23](/[CH3:24])=[CH:19]/[C:9]3[CH:8]=[CH:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=3)[CH:27]=[CH:28][C:29]=2[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19760307HCID 19760307, compoundHCID 88526996HCID 88526996, compound

Product 1

HCID 22990238HCID 22990238, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

770 mg of sodium hydride (50% in mineral oil) are treated at room temperature under an argon atmosphere with 5.30 g of ethyl o-(diethoxyphosphinyl)-p-toluate. After stirring for 2 hours 2.55 g of 2-acetyl-6,7,8,9-tetra-hydro-7 7-dimethyl-5H benzocycloheptene, dissolved in small amount of dimethylformamide, are added dropwise. After 2 hours, the reaction mixture is poured on to ice and extracted with diethyl ether. The ethereal extract is washed with water, dried and evaporated. After chromatography on silica gel with petroleum ether (low-boiling)/ ethyl acetate (9:1), there are obtained 3.40 g of ethyl p-[(E)-2-(6,7,8,9-tetrahydro-7,7-dimethyl-5H-benzocyclo-hepten-2-yl)propenyl]benzoate of m.p. 87-°88° (from hexane).

Workup

  1. additionare added dropwise
  2. additionthe reaction mixture is poured on to ice
  3. extractionextracted with diethyl ether
  4. extractionThe ethereal extract
  5. washis washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-2749875b90354ecc88ad560110bb2f9d
Source dataset
uspto-grants-1991_02
Patent number
US04992574

Reaction notes

Loading…