Methanol → HCID 57508887, compound

HRID 1665933Notes

Reaction equation

HRID 1665933 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)=[O:2].CO>C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Cl-].[Na+].O>[OH:2][CH2:1][C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12

Participants

5

Reactant 2

HCID 887MethanolHCID 574374213-Formyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid

Product 1

HCID 57508887HCID 57508887, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of crude 3-formyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (2.38 g, 10 mmol) in methanol (20 mL) NaBH4 (756 mg, 20 mmol) is added in portions. The mixture is stirred at rt for 15 min, diluted with 10% aq. citric acid and brine and extracted with TBME. The organic extract is dried over Na2SO4 and the solvent is removed under reduced pressure to give 3-hydroxymethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (2.30 g) as a beige foam; LC-MS: tR=0.83 min, [M+1]=241.22; 1H NMR (CDCl3): δ 4.69 (s, 2H), 3.00 (t, J=7.0 Hz, 2H), 2.32 (s, 2H), 1.50 8t, J=7.0 Hz, 2H), 0.94 (s, 6H).

Workup

  1. extractionextracted with TBME
  2. extractionThe organic extract
  3. dry with materialis dried over Na2SO4
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f3f6824271a244a4b6e6a6ca06064229
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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