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Methanol → 3-[4-(tert-Butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester

HRID 1181114
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HRID 1181114 반응식
[C:1]([O:5][C:6](=[O:35])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH:33]=[O:34])([CH3:4])([CH3:3])[CH3:2].C1COCC1.CO.[H][H]>[Pd].C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:11][C:10]=1[CH2:33][OH:34])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 724795813-[4-(tert-Butyldiphenylsilanyloxy)-2-formylphenyl]acrylic acid tert-butyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 589792063-[4-(tert-Butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester

시약·촉매·용매 2

HCID 23938
Palladium
촉매
HCID 8471Triethylamine용매

실험 절차

A 500 mL Parr hydrogenation bottle was charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-formylphenyl]acrylic acid tert-butyl ester (18.3 g, 37.6 mmol), THF (60 mL), and methanol (120 mL). Triethylamine (2 mL) and then 5% Pd/C (5.9 g) were added. The mixture was shaken with hydrogen at 60 psi pressure for 48 h. The mixture was filtered through Celite and concentrated to an oil. This oil was purified using the Biotage medium pressure chromatography (EtOAc:hexanes 15:85) to a pale yellow oil (12.8 g, 69%). 1H NMR (400 MHz, CDCl3) δ 1.09 (s, 9H), 1.35 (s, 9H), 2.49 (t, J=7.6 Hz, 2H), 2.83 (t, J=7.6 Hz, 2H), 4.55 (s, 2H), 6.56 (dd, J=8.3, 2.4 Hz, 1H), 6.83 (d, J=2.9 Hz, 1H), 6.87 (d, J=8.3 Hz, 1H), 7.33-7.44 (m, 6H), 7.70 (dd, J=7.8, 1.5 Hz, 4H). MS (ES) m/e 508 (M+NH4).

후처리

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated to an oil
  3. customThis oil was purified

출처 및 근거

ORD 기록
ord-fd839d474eb24bd7badd52faf2df8abc
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07282501B2

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