Tetrabutylammonium Fluoride → 4-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol

HRID 2253751Notes

Reaction equation

HRID 2253751 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:15][CH:14]=2)[OH:12])=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[OH:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 538578064-(4-Chlorophenyl)-1-(4-t-butyldiphenylsiloxy phenyl)butanol

Product 1

HCID 197458724-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of silyl alcohol (Step V) (1.2 g) in THF (10 mL) and acetic acid (0.3 mL) was added tetrabutylammonium fluoride (3 mL of 1M solution). The reaction mixture was stirred 2 hrs, quenched with pH 7 buffer, extracted with ethyl acetate and the organic extract dried and evaporated. Flash chromatography using 25% ethyl acetate/hexane afforded the title compound.

Workup

  1. customquenched with pH 7 buffer
  2. extractionextracted with ethyl acetate
  3. extractionthe organic extract
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-34d2f6b1aa314a498ed7e136ca26294b
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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