Water → 4-(1-Hydroxypropan-2-yl)-2-methoxybenzonitrile

HRID 1474239Notes

Reaction equation

HRID 1474239 reaction equation
[Li+].[BH4-].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12](OCC)=[O:13])=[CH:7][C:6]=1[O:18][CH3:19])#[N:4].O>C1COCC1>[OH:13][CH2:12][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[C:6]([O:18][CH3:19])[CH:7]=1)[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 66643920Ethyl 2-(4-cyano-3-methoxyphenyl)propanoate

Product 1

HCID 666439114-(1-Hydroxypropan-2-yl)-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (0.55 mL, 1.1 mmol, 2 M in THF) was added to a stirred solution of ethyl 2-(4-cyano-3-methoxyphenyl)propanoate (0.17 g, 0.73 mmol) in THF (25 mL) at 0° C. The resulting solution was stirred for 12 h. Water (15 mL) was added, and the resulting solution was extracted with dichloromethane (2×50 mL). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography eluting with EtOAc-Hexanes (7:3→1:1) to give 4-(1-hydroxypropan-2-yl)-2-methoxybenzonitrile.

Workup

  1. extractionthe resulting solution was extracted with dichloromethane (2×50 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with EtOAc-Hexanes (7:3→1:1)

Sources & evidence

ORD record
ord-d3282151808d4fd8a9d8c2d4353e82f7
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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