Isobutanol → HCID 54757864, compound

HRID 41147Notes

Reaction equation

HRID 41147 reaction equation
[OH:1][C:2]1[CH2:6][CH2:5][C:4](=[O:7])[C:3]=1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][O:17][Si](C(C)C)(C(C)C)C(C)C)[CH:10]=1.[CH2:28](O)[CH:29]([CH3:31])[CH3:30]>C1C=CC=CC=1>[OH:17][CH2:16][CH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:8][C:3]1[C:4](=[O:7])[CH2:5][CH2:6][C:2]=1[O:1][CH2:28][CH:29]([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 6560IsobutanolHCID 547578633-Hydroxy-2-(3-(2-((triisopropylsilyl)oxy)ethyl)benzyl)cyclopent-2-enone

Product 1

HCID 54757864HCID 54757864, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture containing 46 (0.294 g, 0.757 mmol), paratoluensolfonic acid (0.005 g), i-butanol (1.0 mL) and benzene (4.0 mL) was heated to reflux for 12 h. The reaction mixture was then concentrated and the residue so obtained was purified by silica gel column chromatography using 5% of methanol in dichloromethane as eluent, obtaining the desired compound. Yield: 81%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. concentrationThe reaction mixture was then concentrated
  4. customthe residue so obtained
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e18e156ee1644ee4a48f6aade48e5544
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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