Water → HCID 89451901, compound

HRID 1497498Notes

Reaction equation

HRID 1497498 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[C:11]([CH:26]2[CH2:28][CH2:27]2)[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH:26]1([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=2[CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 89451937HCID 89451937, compound

Product 1

HCID 89451901HCID 89451901, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl (4-{[tert-butyl(dimethyl)silyl]oxy}-2-cyclopropylphenyl)acetate (586 mg) in tetrahydrofuran (6.89 mL) was added a 1 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (2.23 mL) under ice-cooling, followed by stirring at room temperature overnight. To a reaction solution was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain benzyl (2-cyclopropyl-4-hydroxyphenyl)acetate (398 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-034305ef1309475781ac7c8fcc7dcdc3
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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