Sodium borohydride → [2-(3-Methylphenyl)tetrahydrofuran-2-yl](pyridin-2-yl)methanol

HRID 1620994Notes

Reaction equation

HRID 1620994 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1([C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[CH2:13][CH2:12][CH2:11][O:10]1)=[O:8].[BH4-].[Na+]>CO>[CH3:20][C:16]1[CH:15]=[C:14]([C:9]2([CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[OH:8])[CH2:13][CH2:12][CH2:11][O:10]2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89524758Pyridin-2-yl(2-m-tolyltetrahydrofuran-2-yl)methanone

Product 1

HCID 71522469[2-(3-Methylphenyl)tetrahydrofuran-2-yl](pyridin-2-yl)methanolYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 91D (478 mg, 1.79 mmol) in methanol (10 mL) was added NaBH4 (135 mg, 3.55 mmol) portion wise, and the mixture was stirred overnight at room temperature. After evaporating most of the solvent, the residue was diluted with 10 mL of water, and extracted with ethyl acetate (15 mL×3). The combined organic phases was dried over Na2SO4, filtered, and concentrated. The residue was purified by prep-TLC (petroleum ether:ethyl acetate=3:1) to give the title compound (182.7 mg, 38%). LC-MS: m/z (M+H): 270. 1H NMR (400 MHz, CDCl3): δ ppm 8.27 (d, J=4.4 Hz, 1H), 6.93-7.59 (m, 7H), 4.83 (d, J=6.0 Hz, 1H), 4.63 (d, J=6.0 Hz, 1H), 3.87-4.07 (m, 2H), 2.60-2.65 (m, 1H), 2.28-2.31 (m, 1H), 2.21 (s, 3H), 1.79-1.92 (m, 2H).

Workup

  1. customAfter evaporating most of the solvent
  2. additionthe residue was diluted with 10 mL of water
  3. extractionextracted with ethyl acetate (15 mL×3)
  4. dry with materialThe combined organic phases was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by prep-TLC (petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ef1f7a4205674b789c13823448d8f6fc
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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