HCID 15723364, compound → HCID 15723379, compound

HRID 654951Notes

Reaction equation

HRID 654951 reaction equation
[C:1]([O:4][CH:5]([C:22]1[CH:23]=[C:24]([Si:27]([CH3:30])([CH3:29])[CH3:28])[O:25][CH:26]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C)C)(=[O:3])[CH3:2]>C(O)(=O)C.O.O1CCCC1>[C:1]([O:4][CH:5]([C:22]1[CH:23]=[C:24]([Si:27]([CH3:30])([CH3:29])[CH3:28])[O:25][CH:26]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 15723364HCID 15723364, compound

Product 1

HCID 15723379HCID 15723379, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

4-(1-Acetoxy-9-t-butyldimethylsiloxynonyl)-2-trimethylsilylfuran (1.00 g, 2.21 mmol) was stirred at 35° for 36 hours in a mixture of acetic acid-water-tetrahydrofuran (1:1:1). The reaction mixture was concentrated and the residue was taken up in ethyl ether, washed with 10% hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to a pale oil. Purification by flash chromatography (silica, 10% ethyl acetate/hexane) gave the desired alcohol.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with 10% hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a pale oil
  6. customPurification by flash chromatography (silica, 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-389f8b0c844440feb4e1e8be125feb1c
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

Loading…