Trimethylsilyl triflate → HCID 59441463, 화합물

HRID 391162노트

반응식

HRID 391162 반응식
[OH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11](=[O:13])[CH3:12])[CH:8]=2)[CH2:3]1.C([Si](C)(C)O[CH:20]1[CH:25]([O:26][CH3:27])[CH:24]([O:28][CH3:29])[CH:23]([O:30][CH3:31])[CH:22]([CH3:32])[O:21]1)(C)(C)C.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH3:27][O:26][C@@H:25]1[C@H:24]([O:28][CH3:29])[C@@H:23]([O:30][CH3:31])[C@H:22]([CH3:32])[O:21][C@H:20]1[O:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11](=[O:13])[CH3:12])[CH:8]=2)[CH2:3]1

참가 물질

5

반응물 3

HCID 65367Trimethylsilyl triflateHCID 59441459HCID 59441459, 화합물HCID 68765652HCID 68765652, 화합물

생성물 1

HCID 59441463HCID 59441463, 화합물수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution at 0-5° C. of 1-(2-hydroxy-indan-5-yl)-ethanone (Compound E-25; 440 mg, 2.50 mmol) and 92% w/w of tert-butyl-dimethyl-(3,4,5-trimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-silane (Compound E-23; 1.00 g, 2.87 mmol) in CH2Cl2 (6 mL) was added via syringe trimethylsilyl triflate (0.12 mL, 146 mg, 0.66 mmol). The contents were allowed to gradually warm to room temperature and were stirred overnight. The solution was diluted with CH2Cl2 and was washed once with saturated sodium bicarbonate (NaHCO3). The aqueous phase was extracted once with CH2Cl2, and the combined organics were dried (MgSO4). Concentration gave a pale green oil (783 mg, 86%): 1H NMR (CDCl3) δ 7.79 (m, 2H), 7.29 (d, J=7.6 Hz, 1H), 4.97 (s, 1H), 4.64 (m, 1H), 3.67-3.40 (m, 3H), 3.55 (s, 3H), 3.50 (s, 3H), 3.45 (s, 3H), 3.21-2.97 (m, 5H), 2.59 (s, 3H), 1.30 (d, J=6.3 Hz, H); IR (neat) 1683 cm−1.

후처리

  1. washwas washed once with saturated sodium bicarbonate (NaHCO3)
  2. extractionThe aqueous phase was extracted once with CH2Cl2
  3. dry with materialthe combined organics were dried (MgSO4)
  4. concentrationConcentration

출처 및 근거

ORD 기록
ord-85334af1273449f681b7d08919b18dba
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383786B2

반응 노트

불러오는 중…