(4S,5S)-4-[(Benzyloxy)methyl]-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane → (2R)-1-(benzyloxy)but-3-en-2-ol
Reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:14]([CH2:15]I)OC(C)(C)[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Zn]>[CH2:1]([O:8][CH2:9][C@H:10]([OH:11])[CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 49.20 g of the crude (4S,5S)-4-[(benzyloxy)methyl]-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane obtained in Reference Example (1c) (136 mmol) and 26.66 g of zinc powder (408 mmol) in ethanol (420 ml) was stirred at 80° C. for three hours. After cooling the reaction mixture, the unreacted zinc powder was separated by filtration using Celite 545 and washed with ethanol. The filtrate was concentrated under reduced pressure and diluted with 1 M hydrochloric acid, followed by extraction with ethyl acetate. Then, the organic layer was washed with water, a 1.5 M sodium sulfite aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 24.29 g of the crude title compound.
Workup
- temperatureAfter cooling the reaction mixture
- customthe unreacted zinc powder was separated by filtration
- washwashed with ethanol
- concentrationThe filtrate was concentrated under reduced pressure
- additiondiluted with 1 M hydrochloric acid
- extractionfollowed by extraction with ethyl acetate
- washThen, the organic layer was washed with water
- dry with materiala 1.5 M sodium sulfite aqueous solution and brine and dried over anhydrous magnesium sulfate
- filtrationAfter filtration
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-f89adf3a876a4cd6b89d681d261aea14
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158790B2
Reaction notes
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