Vinyl Acetate → 3,3-Dimethyl-1-vinyloxybutane
Reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].[C:8](OC=C)(=O)[CH3:9].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][O:5][CH:8]=[CH2:9]Participants
6
Procedure
Add chloro(1,5-cyclooctadiene)iridium(I) dimer (0.39 g, 0.59 mmol) to 3,3-dimethylbutan-1-ol (3.00 g, 29.35 mmol), vinyl acetate (10.11 g, 117.42 mmol) and sodium carbonate (1.87 g, 17.61 mmol) in benzene (10 mL) at room temperature. Boil under nitrogen 12 hours. Cool to room temperature and filter. Distill the filtrate and collect fraction boiling ˜125° C.-130° C. Flush through a silica gel pad with hexanes and concentrate to provide the title compound.
Workup
- custom12 hours
- filtrationfilter
- distillationDistill the filtrate
- customcollect fraction
- customboiling ˜125° C.-130° C
- customFlush through a silica gel pad with hexanes
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-226ce7882d634d20897871d2dacfff1a
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745438B2
Reaction notes
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