Triethylsilane → 1-Triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester

HRID 2070554Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][CH2:6][C:7]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:16]([SiH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][CH2:6][C:7]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:13]1[O:14][Si:18]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:16][CH3:17])=[O:15]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-(1-formyl-cyclohexyl)-but-2-enoic acid methyl ester (3.7 g) obtained in Step 1 and tris(triphenylphosphine) rhodium(I) chloride (163 mg) in toluene (80 mL) was added dropwise triethylsilane (5.9 mL) under argon atmosphere over 10 minutes, followed by stirring the reaction mixture at 55° C. for 27 hours. After cooling down to room temperature and adding aqueous sodium bicarbonate solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=20:1) to give 1-triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester (5.0 g).

Workup

temperatureAfter cooling down to room temperature
extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with water
customdried
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=20:1)

Sources & evidence

ORD record: ord-6a4bf175861b44d8b777ae75cc01aa00
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299296B2

Reaction notes

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