Tetrabutylammonium Fluoride → 1-Hydroxy-2-tetrahydropyranyloxy-2-(4-tert-butylphenyl)ethane

HRID 1516113Notes

Reaction equation

HRID 1516113 reaction equation
[Si]([O:8][CH2:9][CH:10]([O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[OH:8][CH2:9][CH:10]([O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[C:11]1[CH:12]=[CH:13][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 596786401-Tert-butyldimethylsilyloxy-2-tetrahydropyranyloxy-2-(4-tertbutylphenyl) ethane

Product 1

HCID 596787081-Hydroxy-2-tetrahydropyranyloxy-2-(4-tert-butylphenyl)ethane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-tert-butyldimethylsilyloxy-2-tetrahydropyranyloxy-2-(4-tertbutylphenyl)ethane (0.4 g, 1.01 mmol) is added tetrabutylammonium fluoride solution (1M TBAF in THF, 5 ml, 5.0 mmol). The solution is stirred for 2 hours after which water is added to the reaction and this is extracted in ethyl acetate. The organic layer is then washed with water, dried and concentrated. The residue obtained is purified by flash chromatography (silica gel; ethyl acetate/hexanes).

Workup

  1. additionis added to the reaction
  2. extractionthis is extracted in ethyl acetate
  3. washThe organic layer is then washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customis purified by flash chromatography (silica gel; ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1dac8eb011824590be2a021bf671727a
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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