HCID 57443971, compound → HCID 57443968, compound

HRID 548222Notes

Reaction equation

HRID 548222 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-d77b7acfa0364e198fdbf77bb8f80056
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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