HCID 67351277, compound → HCID 67351969, compound

HRID 1676135Notes

Reaction equation

HRID 1676135 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][C:8]([CH3:10])=[CH2:9])=[C:5]([CH3:11])[S:4][C:3]=1[C:12]([OH:14])=O.[CH3:15][Li]>C(OCC)C>[CH3:1][C:2]1[C:6]([CH2:7][C:8]([CH3:10])=[CH2:9])=[C:5]([CH3:11])[S:4][C:3]=1[C:12](=[O:14])[CH3:15]

Participants

4

Reactant 2

HCID 67351277HCID 67351277, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 67351969HCID 67351969, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3,5-dimethyl-4-(2-methyl-allyl)-thiophene-2-carboxylic acid (475 mg, 2.26 mmol) in diethyl ether (15 mL), a solution of methyllithium (3.0 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 (0.45 mL) is added. Stirring is continued for 1 h. The reaction is quenched by the addition of 1 N aq. NaH2PO4 solution. The mixture is diluted with diethyl ether, washed with 1 N aq. NaOH, dried over Na2SO4 and evaporated to give 1-[3,5-dimethyl-4-(2-methyl-allyl)thiophen-2-yl]-ethanone (395 mg) as a yellow oil; LC-MS: tR=1.03 min, [M+1]=209.14.

Workup

  1. additionis added
  2. customThe reaction is quenched by the addition of 1 N aq. NaH2PO4 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-f655e6eb01ba4ad28ff8a1a79d19a6c8
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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