Water → HCID 59511062、化合物

HRID 1011468ノート

反応式

HRID 1011468 の反応式
[N:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])=[N+:2]=[N-:3].C([C:11](CC)(CC)[C:12]([O-])([O-])[O-:13])C.O.CCOC(C)=O>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:12]([O:6][CH2:5][CH:4]([N:1]=[N+:2]=[N-:3])[CH2:7][OH:8])(=[O:13])[CH3:11]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl Acetate2 回HCID 20578392HCID 20578392、化合物HCID 21875354Triethylorthoaceate

生成物 1

HCID 59511062HCID 59511062、化合物収率 57.3%

試薬・触媒・溶媒 2

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

実験手順

2-Azidopropane-1,3-diol 23 (10.46 g, 89.3 mmol) was dissolved in CH2Cl2 (450 mL) and treated with a catalytic amount of p-toluene sulfonic acid monohydrate (340 mg, 1.8 mmol) and triethylorthoacetate (24.4 mL, 134 mmol) at room temperature for 1 hr. After the formation of the orthoester was complete, a stoichiometric amount of water (2.4 mL, 134 mmol) was added to the mixture. The mixture was then stirred for 40 min and then concentrated in vacuo. Purification of the residue on a silica gel cartridge using EtOAc:Hex as the eluent (5% EtOAc to 100% EtOAc) afforded 8.14 g (57% yield) of 24 as a clear, colorless oil. 1H NMR (CDCl3, 400 MHz), δ: 2.45 (1H, br s), 2.12 (3H, s), 3.63-3.78 (3H, 4.20-4.30 (2H, m).

後処理

  1. concentrationconcentrated in vacuo
  2. customPurification of the residue on a silica gel cartridge

出典と根拠

ORDレコード
ord-6c5a93fe776543ca97ae9629b6f29b4d
出典データセット
uspto-grants-2011_07
特許番号
US07977361B2

反応ノート

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