2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 86696655, 화합물

HRID 1774153노트

반응식

HRID 1774153 반응식
[Si:1]([O:8][CH2:9][CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][C:14]=1[F:21]>C1COCC1>[Si:1]([O:8][CH2:9][CH:10]([C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[C:14]([F:21])[CH:15]=1)[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 178505943HCID 178505943, 화합물

생성물 1

HCID 86696655HCID 86696655, 화합물수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of 2-(tert-butyldimethylsilyloxy)acetaldehyde (2.00 g, 10.3 mmol) in dry THF (40 mL) was placed in an ice bath, and (4-chloro-3-fluorophenyl)magnesium bromide (24.8 mL, 12.4 mmol) was added dropwise via a syringe. The reaction mixture was stirred at 0° C. for 1 hour and then carefully quenched by dropwise addition of water. The reaction mixture was concentrated, and the residue was partitioned between EtOAc and saturated aqueous NH4Cl. The organics were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/EtOAc (20:1) to give 2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol (2.92 g, 9.58 mmol, 92.8% yield) as an oil.

후처리

  1. customcarefully quenched by dropwise addition of water
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between EtOAc and saturated aqueous NH4Cl
  4. customThe organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washeluting with hexanes/EtOAc (20:1)

출처 및 근거

ORD 기록
ord-65622ea304ee479ab2103d2977e6b1ba
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09259470B2

반응 노트

불러오는 중…