Water → HCID 67526505, compound

HRID 133779Notes

Reaction equation

HRID 133779 reaction equation
B.O1CCCC1.[F:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[CH2:15][C:16](O)=[O:17].O>C1COCC1>[F:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 193619772-Fluoro-4-hydroxyphenylacetic acid

Product 1

HCID 67526505HCID 67526505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Borane-tetrahydrofuran complex (1.0 M solution in THF, 22 ml, 0.02200 mol) was added dropwise to the solution of (2-fluoro-4-hydroxyphenyl)acetic acid (P. C. Belanger et al. EP 106565 B1, 2.27 g, 0.01145 mol) in dry THF (40 ml) under nitrogen at −10° C., and the resulting solution was stirred for 2 h at −10° C. Water was added and the product was extracted into ethyl acetate. The combined extracts were washed with water, dried and evaporated in vacuo to give the product. 1H NMR (400 MHz, DMSO-d6): 2.62 (2H, t, 3J=7.2 Hz), 3.50 (2H, m), 4.63 (1H, t, 3J=5.4 Hz, —CH2OH), 6.47-6.53 (2H, m), 7.06 (1H, t, 3JHH=4JHF=8.5 Hz), 9.60 (1H, s, ArOH).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried
  4. customevaporated in vacuo
  5. customto give the product

Sources & evidence

ORD record
ord-333c420253fd4210ae65f347c26bc06f
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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