HCID 57508893, compound → HCID 57508895, compound

HRID 2240806Notes

Reaction equation

HRID 2240806 reaction equation
[CH2:1]([C:3]1([CH2:17][CH3:18])[CH2:16][CH2:15][C:6]2=[C:7]([C:12]([OH:14])=O)[S:8][C:9]([S:10][CH3:11])=[C:5]2[CH2:4]1)[CH3:2].[CH3:19][Li]>C(OCC)C>[CH2:17]([C:3]1([CH2:1][CH3:2])[CH2:16][CH2:15][C:6]2=[C:7]([C:12](=[O:14])[CH3:19])[S:8][C:9]([S:10][CH3:11])=[C:5]2[CH2:4]1)[CH3:18]

Participants

4

Reactant 2

HCID 57508893HCID 57508893, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 57508895HCID 57508895, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 5,5-diethyl-3-methylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (669 mg, 2.35 mmol) in diethyl ether (20 mL), a solution of methyllithium (2.6 mL, 1.6 M in diethyl ether) is added at rt. The reaction mixture is stirred at rt for 4 h, diluted with diethyl ether, washed with 1 N aq. K2HPO4 solution followed by 1 N aq. NaOH, dried over Na2SO4 and evaporated to give 1-(5,5-diethyl-3-methylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (458 mg) as a yellow oil, LC-MS: tR=1.15 min, [M+1]=283.1; 1H NMR(CDCl3): δ 2.96 (t, J=7.0 Hz, 2H), 2.53 (s, 3H), 2.45 (s, 3H), 2.32 (s, 2H), 1.56 (t, J=7.0 Hz, 2H), 1.35-1.20 (m, 4H), 0.83 (t, J=7.6 Hz, 6H).

Workup

  1. washwashed with 1 N aq. K2HPO4 solution
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-aef89ea0ae41462eb475aa5941e6467b
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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