HCID 19595656, compound → HCID 54397734, compound

HRID 612733Notes

Reaction equation

HRID 612733 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2([CH3:15])[CH3:14])=[C:7]([C:16]2([CH2:19][CH:20]=O)[CH2:18][CH2:17]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:22]([O:24][C:25]([CH:27]=[C:28]([CH3:34])[CH2:29]P(=O)([O-])[O-])=[O:26])[CH3:23]>>[CH2:22]([O:24][C:25](=[O:26])[CH:27]=[C:28]([CH3:34])[CH:29]=[CH:20][CH2:19][C:16]1([C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][C:11]3([CH3:14])[CH3:15])[CH2:18][CH2:17]1)[CH3:23]

Participants

3

Reactant 2

HCID 19595656HCID 19595656, compoundHCID 86754974HCID 86754974, compound

Product 1

HCID 54397734HCID 54397734, compoundYield 69%

Procedure

The above unsaturated alcohol (16) (30 mg, 0.16 mmol) was converted to the cyclopropyl alcohol as described in Example 1 to give 33 mg of [1-(6-t-butyl-1,1-dimethyl-indan-4-yl)-cyclopropyl]-ethanol (17) as a pale yellow oil in 67% yield that was used directly for the next step. The above cyclopropyl alcohol (33 mg, 0.15 mmol) was oxidized as described in Example 1 to give 32 mg of 1-(6-t-butyl-1,1-dimethyl-indan-4-yl)-cyclopropaneacetaldehyde (18) as a clear oil in 100% yield. The above cyclopropyl aldehyde 18 (32 mg, 0.15 mmol) and 3-ethoxycarbonyl-2-methylprop-2-enylphosphonate (200 mg, 0.77 mmol) were condensed as described for Example 1 to give 37 mg of ethyl-6-[1-(6-t-butyl-1,1-dimethyl-indan-4-yl)-cyclopropyl]-3-methyl-2,4-hexadienoate (19) as a pale yellow oil in 69% yield.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-c3b53d65d1124d658c7be3fdcef45613
Source dataset
uspto-grants-1999_12
Patent number
US06005007

Reaction notes

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