Water → HCID 46836904, compound

HRID 445895Notes

Reaction equation

HRID 445895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:27])[C:24]([OH:26])=[O:25])=[CH:18][C:17]=2[F:28])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[C:6]=2[CH:13]=1.[BH4-].[Na+].O>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:27])[C:24]([OH:26])=[O:25])=[CH:18][C:17]=2[F:28])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([OH:12])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 46836843HCID 46836843, compound

Product 1

HCID 46836904HCID 46836904, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3-(4-((5-chloro-2,2-dimethyl-3-oxo-2,3-dihydrobenzofuran-7-yl)methoxy)-3-fluorophenyl)-2-methylpropanoic acid (106) (80 mg, 0.197 mmol) in tetrahydrofuran/methanol (2:1, 2 mL) was added sodium borohydride (15 mg, 0.393 mmol). After the reaction was stirred at room temperature for 1.5 hours water was added and the solution was extracted with ethyl acetate, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield 3-(4-((5-chloro-3-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-3-fluorophenyl)-2-methylpropanoic acid (109). 1H NMR (400 MHz, CDCl3) δ 7.40 (s, 1H), 7.31 (s, 1H), 6.92 (m, 2H), 6.82 (d, J=12.0 Hz, 1H), 5.04 (s, 2H), 4.75 (s, 1H), 2.93 (m, 1H), 2.71 (m, 1H), 2.64 (m, 1H), 1.49 (s, 3H), 1.34 (s, 3H), 1.18 (d, J=6.9 Hz, 3H). LC-MS ESI m/z: found 407.3 [M−H]−.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2524664ae58e43ab9308313d0c7efeee
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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