Water → HCID 14650424, 화합물

HRID 1199914노트

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HRID 1199914 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 14650424HCID 14650424, 화합물수율 78.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c21fd946a0ea42eeafc51b46e2044daf
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904654

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