Water → HCID 59511065、化合物

HRID 1157095ノート

反応式

HRID 1157095 の反応式
[N:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])=[N+:2]=[N-:3].C[O:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(OC)OC.O>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:11]([O:6][CH2:5][CH:4]([N:1]=[N+:2]=[N-:3])[CH2:7][OH:8])(=[O:10])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 962WaterHCID 69720Trimethyl orthobeznoateHCID 20578392HCID 20578392、化合物

生成物 1

HCID 59511065HCID 59511065、化合物収率 93%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Neat 23 (1.48 g, 12.65 mmol) was dissolved in CH2Cl2 (127 mL) and treated with a catalytic amount of p-toluene sulfonic acid monohydrate (0.048 g, 20 μmol) and (trimethoxymethyl)benzene (3.26 mL, 18.98 mmol) in CH2Cl2 at room temperature for 1 hr. After the formation of the orthoester was complete, a stoichiometric amount of water (340 μL, 18.98 mmol) was added to the mixture. The mixture was then stirred for 40 min and concentrated in vacuo. Purification of the residue by silica gel flash chromatography using 25% EtOAc/hexanes gave 2.6 g of monoacylated product 27 (93% yield) as a clear, colorless oil. 1H NMR (CDCl3, 400 MHz) δ: 8.03-8.06 (m, 2H), 7.58 (tt, J=1.6, 2.0, 1.6 1H), 7.43-7.47 (m, 2H), 4.54 (dd, J=4.4, 12.0 Hz, 1H), 4.46 (dd, J=6.8, 12.0 Hz, 1H), 3.85-3.91 (m, 1H), 3.80 (dd, J=4.8, 11.6 Hz, 1H), 3.73 (dd, J=6.0, 11.6 Hz, 1H).

後処理

  1. concentrationconcentrated in vacuo
  2. customPurification of the residue by silica gel flash chromatography

出典と根拠

ORDレコード
ord-ed4abaafdc3f41e5a5c5b294c4bc9051
出典データセット
uspto-grants-2010_10
特許番号
US07807394B2

反応ノート

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