HCID 57443971, compound → HCID 57443968, compound

HRID 1011646Notes

Reaction equation

HRID 1011646 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([C:15](O)=[O:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5]>C1COCC1>[CH2:2]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH2:15][OH:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:1]

Participants

3

Reactant 1

HCID 57443971HCID 57443971, compound

Product 1

HCID 57443968HCID 57443968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester (332 mg, 1.32 mmol) in 5 mL of anhydrous THF at 0 degrees Celsius was slowly added BH3. The resulting mixture was allowed to stir at 0 degrees Celsius for 30 mins and at rt overnight. After cooling to 0 degrees Celsius, the reaction mixture was quenched with 1N HCl. Additional 120 mL of water was added and THF was removed in vacuo. The solid was filtered and washed with water. After drying, 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester was obtained as pale solid (229 mg, 73.2%). MS: calc'd 237 (MH+), exp 237 (MH+). 1H NMR (CDCl3, 400 MHz), 8.04 (s, 1H), 7.88 (s, 1H), 7.85 (d, 1H, J=8.4 Hz), 7.40 (d, 1H, J=8.0 Hz), 4.42 (q, 2H, J=7.2 Hz), 1.43 (t, 3H, J=7.2 Hz).

Workup

  1. customat 0 degrees Celsius
  2. temperatureAfter cooling to 0 degrees Celsius
  3. customthe reaction mixture was quenched with 1N HCl
  4. additionAdditional 120 mL of water was added
  5. customTHF was removed in vacuo
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customAfter drying

Sources & evidence

ORD record
ord-0b2c316c33c04e75827f1ba51ce2cc8c
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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