Triethylamine → Methyl-9-t-butyldiphenylsilyloxy-nonanoate

HRID 47186

반응식

HRID 47186 반응식
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].CCN(CC)CC.[C:21]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])([CH3:23])[CH3:22].[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 292983Nonanoic acid, 9-hydroxy-, methyl ester

생성물 1

HCID 11133704Methyl-9-t-butyldiphenylsilyloxy-nonanoate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

A solution of methyl-9-hydroxy-nonanoate (0.838 g, 4.46 mmol, 1.0 equiv: Aldrich) in CH2Cl2 (15 mL, 0.3 M) was treated successively with Et3N (0.75 mL, 5.38 mmol, 1.2 equiv), t-butylchlorodiphenylsilane (1.28 mL, 4.93 mmol, 1.1 equiv), and DMAP (0.180 g, 1.48 mmol, 0.33 equiv), and the reaction mixture was stirred at 25° C. for 12 h. Saturated aqueous NH4Cl was added to the reaction mixture and the mixture was partitioned between CH2Cl2 (100 mL) and H2O (100 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Chromatography (SiO2, 5 cm×15 cm, 0-5% EtOAc-hexanes gradient elution) afforded the intermeidate as a clear, colorless oil (1.22 g, 1.831 theoretical, 64.1%): 1H NMR (CDCl3, 250 MHz) δ 7.66 (m, 4H, ArH), 7.38 (m, 6H, ArH), 3.67-3.62 (m, 5H, C(O)OCH3 and CH2OTBDPS), 2.30 (t, 2H, J=7.4 Hz, CH2C(O)OCH3), 1.58 (m, 4H, CH2CH2OTBDPS and CH2CH2C(O)OCH3), 1.28 (b s, 8H, alkyl protons), 1.05 (s, 9H, C(CH3)3).

후처리

  1. customthe mixture was partitioned between CH2Cl2 (100 mL) and H2O (100 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. washChromatography (SiO2, 5 cm×15 cm, 0-5% EtOAc-hexanes gradient elution)
  5. customafforded the intermeidate as a clear, colorless oil (1.22 g, 1.831 theoretical, 64.1%)

출처 및 근거

ORD 기록
ord-173eb6b3354c4379ad031ac6b136d362
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699682B2

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