HCID 57437423, compound → HCID 57508888, compound

HRID 1665934Notes

Reaction equation

HRID 1665934 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:18][CH3:19])=[C:9]2[C:14](=O)[C:13]([CH3:17])([CH3:16])[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]>C(Cl)Cl.C(OCC)C.[Zn+2].[I-].[I-]>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:18][CH3:19])=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:17])[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 57437423HCID 57437423, compound

Product 1

HCID 57508888HCID 57508888, compound

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalyst2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of anhydrous ZnI2 (647 mg, 2.03 mmol) and Na(BH3CN) (117 mg, 1.86 mmol) in DCM (5 mL), a solution of 5,5-dimethyl-3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid ethyl ester (539 mg, 1.81 mmol) in DCM (5 mL) is added. The yellow suspension is refluxed over night before another portion of ZnI2 (100 mg, 0.314 mmol) and Na(BH3CN) (26 mg, 0.419 mmol) is added. The reaction mixture is refluxed for further 24 h. The mixture is diluted with diethyl ether and washed with sat. aq. NaHCO3 solution and brine. The organic layer is separated, dried over Na2SO4 and the solvent is removed under reduced pressure to give 5,5-dimethyl-3-methylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid ethyl ester as a beige resin; LC-MS: tR=1.15 min, [M+1]=285.2; 1H NMR (CDCl3): δ 4.30 (q, J=7.0 Hz, 2H), 3.00 (t, J=7.0 Hz, 2H), 2.50 (s, 3H), 2.33 (s, 3H), 1.54 (t, J=7.0 Hz, 2H), 1.35 (t, J=7.0 Hz, 3H), 0.97 (s, 6H).

Workup

  1. additionis added
  2. temperatureThe reaction mixture is refluxed for further 24 h
  3. washwashed with sat. aq. NaHCO3 solution and brine
  4. customThe organic layer is separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-fc7412125b53410c87b0abc8533ce7f2
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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