Cyclopropanol → HCID 19595644, compound

HRID 612729Notes

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

Reactant 2

HCID 123361Cyclopropanol

HCID 19595662HCID 19595662, compound

Product 1

HCID 19595644HCID 19595644, compoundYield 91%

Procedure

The above unsaturated alcohol 8 (930 mg, 4.55 mmol) was converted to the cyclopropyl alcohol as described in Example 1 to give 900 mg of [1-(3,4-diethyl benzene)-cyclopropyl]-ethanol (9) as a pale yellow oil in 91% yield. The above cyclopropyl alcohol (900 mg, 4.12 mmol) was oxidized as described in Example 1 to give 520 mg of 1-(3,4-diethyl benzene) cyclopropaneacetaldehyde (10) as a clear oil in 58% yield. 1H NMR (400 MHz, CDCl3) δ9.77 (t, J=2.5 Hz, 1H, aldehyde), 7.08 (m, 3H, aromatic), 2.62 (m, 4H, aliphatic 2CH2), 2.59 (d, J=2.8 Hz, 2H, aliphatic CH2), 1.20 (m, 6H, aliphatic, 2CH3), 1.02 (dd, J=6.3, 4.9 Hz, 2H, aliphatic CH2), 0.87 (dd, J=6.0, 4.4 Hz, 2H, aliphatic CH2).

Sources & evidence

ORD record: ord-2092c6a59abd41f1b2d9afa581d6c316
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06005007

Reaction notes

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