Sodium cyanoborohydride → 4-(2,2,2-Trifluoro-1-hydroxyethyl)phenol

HRID 1009168Notes

Reaction equation

HRID 1009168 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].C([BH3-])#N.[Na+]>ClC(Cl)C.[I-].[Zn+2].[I-]>[F:1][C:2]([F:12])([F:13])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 114468182,2,2-Trifluoro-1-(4-hydroxyphenyl)ethanone

Product 1

HCID 112869774-(2,2,2-Trifluoro-1-hydroxyethyl)phenol

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethanone (5.0 g, 26 mmol) in dichloroethane was added zinc iodide (2.7 ml, 39 mmol) followed by sodium cyanoborohydride (10 ml, 197 mmol). The reaction was stirred at RT for 18 h. Both TLC and LCMS showed one product was formed. MS+=175 (desired mass 192-OH). The mixture was filtered through celite and rinsed with dichloromethane. The filtrate was concentrated and dried in vacuum to afford the title compound as colorless oil. MS m/z: 175(M−H2O).

Workup

  1. customwas formed
  2. filtrationThe mixture was filtered through celite
  3. washrinsed with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customdried in vacuum

Sources & evidence

ORD record
ord-6fb2957f8801473f8ec7a656fb150348
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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