Ethanol → 1-(5,5-Dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

HRID 1665939Notes

Reaction equation

HRID 1665939 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:13][CH2:12][C:5]2=[C:6]([C:9]([OH:11])=O)[S:7][CH:8]=[C:4]2[CH2:3]1.[CH2:15](O)C>C(OCC)C.C1COCC1.C[Li].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:14][C:2]1([CH3:1])[CH2:13][CH2:12][C:5]2=[C:6]([C:9](=[O:11])[CH3:15])[S:7][CH:8]=[C:4]2[CH2:3]1

Participants

7

Reactant 2

HCID 702EthanolHCID 57508882HCID 57508882, compound

Product 1

HCID 575088941-(5,5-Dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

Reagents, catalysts & solvents 4

HCID 311Citric AcidSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 178418348HCID 178418348, compoundSolvent

Procedure

To a solution of 5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (1051 mg, 5.0 mmol) in diethyl ether (15 mL) and THF (8 mL), methyllithium (7 mL of a 1.6 M solution in diethyl ether) is added. The mixture is stirred at rt for 15 min before the reaction is queched with ethanol. The mixture is diluted with 10% aq. citric acid and extracted with TBME. The organic extract is washed three times with sat. aq. NaHCO3, dried over Na2SO4 and evaporated to give crude 1-(5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (1.0 g) as a brownish oil; LC-MS: tR=1.03 min, [M+1]=209.07.

Workup

  1. extractionextracted with TBME
  2. extractionThe organic extract
  3. washis washed three times with sat. aq. NaHCO3
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-91b3ddb673864d179a06795f6e684eeb
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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