HCID 57443971, compound → HCID 57443968, compound

HRID 2360618Notes

Reaction equation

HRID 2360618 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, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester (1.6 g, 6.4 mmol) in anhydrous THF (40 mL, 25 vol) was cooled to 0° C. To this BH3 (1M in THF, 30 mL, 30.0 mmol) was added slowly. The reaction was allowed to warm to r.t. and stirred for 3 h. The solution was then cooled to 0° C. and quenched using 1N HCl (7.5 mL). The reaction mixture was concentrated under vacuum to remove all THF and the resulting solid isolated by filtration and dried under vacuum to give 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester (1.3 g, 87%). LCMS m/z 237 [M++H]+, 1H NMR (300 MHz, DMSO), δ: 1.34 (3H, t J=6.9 Hz, CH3), 4.35 (2H, q J=7.1 Hz, CH2), 4.65 (2H, s, CH2), 6.53 (1H, br s, OH), 7.42 (1H, d J=9.4 Hz), 7.98 (3H, m, ArH), 8.18 (1H, s, ArH).

Workup

  1. temperatureThe solution was then cooled to 0° C.
  2. customquenched
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto remove all THF
  5. customthe resulting solid isolated by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-680e88ba08a9475c82ebd0f90d1dd7cd
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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