Water → HCID 14650424、化合物

HRID 1199914ノート

反応式

HRID 1199914 の反応式
[CH3:1][O:2][C:3](=[O:8])[C:4]([OH:7])([CH3:6])[CH3:5].O([Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])S(C(F)(F)F)(=O)=O.N1C(C)=CC=CC=1C.O>C(Cl)Cl>[Si:17]([O:7][C:4]([CH3:6])([CH3:5])[C:3]([O:2][CH3:1])=[O:8])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

参加物

6

反応物 4

HCID 962WaterHCID 79372,6-LutidineHCID 75024Methyl alpha-hydroxyisobutyrateHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

生成物 1

HCID 14650424HCID 14650424、化合物収率 78.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred, chilled (0° C.) solution of methyl-2-hydroxyisobutyrate (20.0 g) in dry CH2Cl2 was added TBDMS triflate (45 g) dropwise, followed by anhydrous 2,6-lutidine (19.3 g). The mixture was stirred at 0° C. for 1 hour before 150 ml water was added. Stirring was continued for a further hour, the organic layer separated, dried (Na2SO4), and concentrated to dryness at reduced pressure. The crude product was purified by dry flash silica gel chromatography eluting with CH2Cl2 to yield the title compound as a colorless oil (30.9 g). δH (360 MHz, CDCl3) 0.07 (6H, s, Si(CH3)2), 0.87 (9H, s, C(CH3)3), 1.41 (6H, s, C(CH3)2), 3.69 (3H, s, CH3O). m/z 233 (M+1)+, 100%, CI+) 217 (30), 174 (40), 164 (45), 106 (30).

後処理

  1. additionwas added
  2. waitwas continued for a further hour
  3. customthe organic layer separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness at reduced pressure
  6. customThe crude product was purified
  7. customby dry flash silica gel chromatography
  8. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-c21fd946a0ea42eeafc51b46e2044daf
出典データセット
uspto-grants-1990_02
特許番号
US04904654

反応ノート

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