HCID 68724543, compound → HCID 68725039, compound

HRID 1471412Notes

Reaction equation

HRID 1471412 reaction equation
C1C2(CCCC=C2C(=O)C)CC=C1.O[CH:15]([CH3:29])[CH2:16][C:17]([C:19]1[C:20]2([CH2:25][CH2:26][CH2:27][CH:28]=1)[CH2:24][CH:23]=[CH:22][CH2:21]2)=[O:18].CC(OC(C)=O)=O.C(O[Na])(C)=O>CCCCCC.CC(OC)(C)C>[CH2:24]1[C:20]2([CH2:25][CH2:26][CH2:27][CH:28]=[C:19]2[C:17](=[O:18])/[CH:16]=[CH:15]/[CH3:29])[CH2:21][CH:22]=[CH:23]1

Participants

5

Reactant 3

HCID 68724543HCID 68724543, compoundHCID 68726783HCID 68726783, compoundHCID 178476463HCID 178476463, compound

Product 1

HCID 68725039HCID 68725039, compound

Reagents, catalysts & solvents 1

HCID 21982663Methyl t-butylether hexaneSolvent

Procedure

Prepared as described in Example 10, from 1-(spiro[4.5]deca-2,6-dien-6-yl)ethanone via 3-hydroxy-1-(spiro[4.5]deca-2,6-dien-6-yl)butan-1-one (LDA, acetaldehyde, THF, 72% after FC (SiO2, hexane/MTBE 1:1); 17% starting material recovered) and subsequent Ac2O/AcONa treatment (35% after FC (SiO2, hexane/MTBE 30:1)). Boiling point: 110° C. (0.08 mbar).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-23fbe3618f0745deb5f321fe0fa91316
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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