Cyclopropanol → HCID 19595644, compound
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[CH2:19])[CH2:16]CO)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH:20]1([OH:23])C[CH2:21]1>>[C:11]([C:9]1[CH:8]=[C:7]([C:15]2([CH:20]([OH:23])[CH3:21])[CH2:19][CH2:16]2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)([CH3:12])([CH3:13])[CH3:14]Participants
Procedure
The above unsaturated alcohol 8 (70 mg, 0.34 mmol) was converted to the cyclopropyl alcohol as described in Example 1 to give 29 mg of [1-(3,5-di-t-butyl phenyl)-cyclopropyl]-ethanol (9) as a pale yellow oil in 40% yield. 1H NMR (400 MHz, CDCl3) δ7.25 (d, J=1.8 Hz, 1H, aromatic), 7.15 (d, J=1.8 Hz, 2H, aromatic), 3.65 (q, J=12.5, 6.7 Hz, 2H, aliphatic CH2), 1.83 (t, J=6.9 Hz, 2H, aliphatic CH2), 1.31 (s, 18H, aliphatic 6CH2), 1.18 (t, J=5.6 Hz, 1H, alcohol), 0.84 (dd, J=9.9, 4.5 Hz, 2H, aliphatic CH2), 0.71 (dd, J=10.0, 3.9 Hz, 2H, aliphatic CH2). The above cyclopropyl alcohol (29 mg, 0.13 mmol) was oxidized as described in Example 1 to give 29 mg of 1-(3,5-di-t-butyl phenyl)-cyclopropaneacetaldehyde (10) as a clear oil in 100% yield. 1H NMR (400 MHz, CDCl3) δ9.79 (t, J=2.6 Hz, 1H, aldehyde), 7.25 (s, 1H, aromatic), 7.12 (d, J=1.3 Hz, 2H, aromatic), 2.59 (d, J=2.5 Hz, 2H, aliphatic CH2), 1.31 (s, 18H, aliphatic 6CH2), 1.04 (dd, J=10.7, 5.2 Hz, 2H, aliphatic CH2), 0.88 (dd, J=10.6, 5.5 Hz, 2H, aliphatic CH2).
Sources & evidence
- ORD record
- ord-c5a60003a8ec4d04a381952e098ad10d
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06005007
Reaction notes
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