Sodium borohydride → HCID 86696516, compound

HRID 1615919Notes

Reaction equation

HRID 1615919 reaction equation
[BH4-].[Na+].[CH:3]([CH:5]1[CH2:7][CH:6]1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11])=[O:4]>C(Cl)Cl.CO>[OH:4][CH2:3][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86696514HCID 86696514, compound

Product 1

HCID 86696516HCID 86696516, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Solid sodium borohydride (110 mg, 2.92 mmol) was added portionwise to a solution of 2-(2-formylcyclopropyl)benzonitrile (500 mg, 2.92 mmol) in methylene chloride (6 mL) and MeOH (10 mL). The mixture was stirred for 2 hr. The reaction was concentrated, and the residue was dissolved in ether and water. The ether layer was separated, washed with water and brine, dried over magnesium sulfate, and concentrated to give 2-(2-(hydroxymethyl)cyclopropyl)benzonitrile as a slightly colored wax (425 mg, 84%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.63 (dd, J=7.7, 0.9 Hz, 1H), 7.52 (td, J=7.8, 1.0 Hz, 1H), 7.36-7.24 (m, 1H), 7.08 (d, J=8.0 Hz, 1H), 3.87-3.72 (m, 1H), 3.65 (dd, J=11.2, 7.2 Hz, 1H), 2.25-2.13 (m, 1H), 1.82 (br. s., 1H), 1.60 (s, 1H), 1.56-1.45 (m, 1H), 1.12 (ddt, J=15.3, 8.6, 5.3 Hz, 1H). LCMS: M+1=173.1.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in ether
  3. customThe ether layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15f01af962564e66b5971d67edae3d0b
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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