HCID 57508889, compound → HCID 57437426, compound

HRID 2240805Notes

Reaction equation

HRID 2240805 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:15][CH2:14][C:5]2=[C:6]([C:11]([OH:13])=O)[S:7][C:8]([S:9][CH3:10])=[C:4]2[CH2:3]1.[CH3:17][Li]>C(OCC)C>[CH3:16][C:2]1([CH3:1])[CH2:15][CH2:14][C:5]2=[C:6]([C:11](=[O:13])[CH3:17])[S:7][C:8]([S:9][CH3:10])=[C:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 57508889HCID 57508889, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 57437426HCID 57437426, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5,5-dimethyl-3-methylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (508 mg, 1.98 mmol) in diethyl ether (20 mL), a solution of methyllithium (1.1 mL, 1.6 M in diethyl ether) is added at rt. The mixture is stirred at rt for 1 h before another portion of methyllithium (0.25 mL) is added. Stirring is continued for 2 h. The reaction is quenched by the addition of 1 N aq. K2HPO4 solution. The mixture is diluted with diethyl ether, washed with 1 N aq. NaOH, dried over Na2SO4 and evaporated to give 1-(5,5-dimethyl-3-methylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (214 mg) as a yellow oil; LC-MS: tR=1.09 min, [M+1]=255.1.

Workup

  1. additionis added
  2. customThe reaction is quenched by the addition of 1 N aq. K2HPO4 solution
  3. additionThe mixture is diluted with diethyl ether
  4. washwashed with 1 N aq. NaOH
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-64c0ed77c1304e64933401907c8b0da5
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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