HCID 57443971, compound → HCID 57443968, compound

HRID 1172852Notes

Reaction equation

HRID 1172852 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 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester (6.40 g, 25.57 mmol) in 250 mL of anhydrous THF at 0° C. was slowly added BH3 (1.5 M in THF, 80.0 mL, 120 mmol). The resulting mixture was allowed to stir at 0° C. for 30 min and at rt overnight. After cooling to 0° C., the reaction mixture was quenched with 1N HCl (30 mL). Additional 120 mL of water was added and THF was removed in vacuo. The solid formed was filtered and washed with 2×20 mL of water. After drying, 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester was obtained as pale solid. 1H NMR (CDCl3, 200 MHz) δ 8.00 (s, 1H), 7.88-7.76 (m, 2H), 7.36 (d, J=9.4 Hz, 1H), 4.80 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 2.00 (brs, 1H), 1.39 (t, J=7.0 Hz, 3H). MS (EI): cal'd 237.0 (MH+), exp 237.1 (MH+).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction mixture was quenched with 1N HCl (30 mL)
  3. additionAdditional 120 mL of water was added
  4. customTHF was removed in vacuo
  5. customThe solid formed
  6. filtrationwas filtered
  7. washwashed with 2×20 mL of water
  8. customAfter drying

Sources & evidence

ORD record
ord-50d71ab88440458992985232203c8ca4
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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