Methanol → HCID 57540555, compound

HRID 2059872Notes

Reaction equation

HRID 2059872 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[C:4]([O:15][CH3:16])[CH:3]=1.CO.[BH4-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH:8]([CH:10]2[CH2:11][CH2:12]2)[OH:9])=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58579838HCID 58579838, compound

Product 1

HCID 57540555HCID 57540555, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromo-2-methoxyphenoxy)-1-cyclopropylethanone Part B (1.7 g, 5.96 mmol) in THF (12 mL) and MeOH (12 mL) was slowly added sodium borohydride (0.226 g, 5.96 mmol). After stirring at RT for 30 min, the mixture was concentrated, diluted with EtOAc, washed with sat NaHCO3, 1N HCl, brine, dried (Na2SO4) and concentrated. The crude product was purified using ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4-bromo-2-methoxyphenoxy)-1-cyclopropylethanol 16C (1.53 g, 5.33 mmol, 89% yield) as a clear oil. 1H NMR (400 MHz, chloroform-d) δ 6.97-7.07 (2H, m), 6.81 (1H, d, J=8.53 Hz), 4.14 (1H, dd, J=9.79, 2.76 Hz), 3.90-3.98 (1H, m), 3.85 (3H, s), 3.31 (1H, t, J=2.51 Hz), 2.78 (1H, s), 0.88-1.01 (1H, m), 0.49-0.67 (2H, m), 0.44 (1H, dd, J=9.41, 4.64 Hz), 0.25-0.33 (1H, m).

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-763696df9f9f4ad8895973616b0643d1
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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