2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 86696655、化合物

HRID 1774153ノート

反応式

HRID 1774153 の反応式
[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]

参加物

4

反応物 2

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 178505943HCID 178505943、化合物

生成物 1

HCID 86696655HCID 86696655、化合物収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-65622ea304ee479ab2103d2977e6b1ba
出典データセット
uspto-grants-2016_02
特許番号
US09259470B2

反応ノート

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