Water → Ethyl 3-(3-(hydroxymethyl)phenyl)hex-4-ynoate

HRID 1049561Notes

Reaction equation

HRID 1049561 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][CH2:37][C:38]1[CH:39]=[C:40]([CH:44]([C:51]#[C:52][CH3:53])[CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH:41]=[CH:42][CH:43]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.O>C1COCC1>[OH:36][CH2:37][C:38]1[CH:39]=[C:40]([CH:44]([C:51]#[C:52][CH3:53])[CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131736028Ethyl 3-(3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)hex-4-ynoate

Product 1

HCID 117760135Ethyl 3-(3-(hydroxymethyl)phenyl)hex-4-ynoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (5.0 mL) of tetrabutylammonium fluoride in THF was added to a solution of ethyl 3-(3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)hex-4-ynoate in THF (10 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (181 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-942e3f89e60247858be302fc67f3f8a7
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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