Trimethylsilyl triflate → HCID 59441463、化合物

HRID 391162ノート

反応式

HRID 391162 の反応式
[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

参加物

5

反応物 3

HCID 65367Trimethylsilyl triflateHCID 59441459HCID 59441459、化合物HCID 68765652HCID 68765652、化合物

生成物 1

HCID 59441463HCID 59441463、化合物収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-85334af1273449f681b7d08919b18dba
出典データセット
uspto-grants-2013_02
特許番号
US08383786B2

反応ノート

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