Hydrochloric Acid → 3-{3-[2-Hydroxy-2-(5-phenyl-furan-2-yl)-ethyl]-phenyl}-acrylic acid

HRID 659109Notes

Reaction equation

HRID 659109 reaction equation
[O:1]=[C:2]([C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1.[BH4-].[Na+].Cl>CO>[OH:1][CH:2]([C:15]1[O:16][C:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:18][CH:19]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 684146653-(3-[2-Oxo-2-(5-phenyl-furan-2-yl)-ethyl]-phenyl)-acrylic acid

Product 1

HCID 684146793-{3-[2-Hydroxy-2-(5-phenyl-furan-2-yl)-ethyl]-phenyl}-acrylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ketone (27) (33 mg; 0.10 mmol) dissolved in MeOH (2 mL) was added sodium borohydride (8 mg, 0.21 mmol). Subsequent additions of sodium borohydride (2 mg) were added until the reaction was complete. The reaction mixture was acidified to pH 5 by dropwise addition of 1N HCl and extracted with TBME (×3). The organic layer was dried (MgSO4) and the solvent concentrated in vacuo to give the title compound as a white solid. Yield: 20 mg, 61%; LC-MS tr 2.02 min; HPLC Purity: 100%; MS (ES+) m/z 335 (M+H), 317 (M−H2O+H); 1H NMR (400 MHz; CDCl3): δ 3.20-3.30 (d, 2H), 5.0 (t, 1H), 6.3 (d, 1H), 6.40 (d, 1H), 6.60 (d, 1H), 7.20-7.50 (m, 7H), 7.65-7.80 (m, 3H)

Workup

  1. extractionextracted with TBME (×3)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationthe solvent concentrated in vacuo

Sources & evidence

ORD record
ord-8a88aa63a3d24f8d9c0731b675217282
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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