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

HRID 2070554노트

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HRID 2070554 반응식
[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]

참가 물질

6

반응물 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 727655614-(1-Formyl-cyclohexyl)-but-2-enoic acid methyl ester

생성물 1

HCID 577713731-Triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 178479813HCID 178479813, 화합물촉매HCID 1140Toluene용매

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온도
55 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-6a4bf175861b44d8b777ae75cc01aa00
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299296B2

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