Dimethylformamide → 3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde

HRID 471171

反応式

HRID 471171 の反応式
[C:1]([Si:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CN(C)CCN(C)CCN(C)C.CN(C)[CH:37]=[O:38]>C1COCC1>[Si:5]([O:8][CH2:9][CH2:10][C:11]1[C:12]([F:17])=[C:13]([CH:14]=[CH:15][CH:16]=1)[CH:37]=[O:38])([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:6])[CH3:7]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 18196PentamethyldiethylenetriamineHCID 57988979tert-Butyl(2-fluorophenethoxy)dimethylsilaneHCID 178418400CID 53628100

生成物 1

HCID 579891643-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

tert-Butyl(2-fluorophenethoxy)dimethylsilane (example 78, step a) (5.00 g) was added over 5 minutes to a stirred solution of sec-butyllithium (1.4 molar solution in cyclohexane, 14.0 mL) and N1-(2-(dimethylamino)ethyl)-N1,N2,N2-trimethylethane-1,2-diamine (4.10 mL) in THF (25 mL) cooled to −78° C. After 2 h, N,N-dimethylformamide (10.06 g) was added, the reaction mixture was stirred at −78° C. for 1 h, and then the cooling bath was removed. After a further 0.5 h, the reaction was quenched with water. Ethyl acetate (300 mL) was added and the reaction mixture washed with water (3×150 mL), 2M HCl (2×50 mL), water (2×50 mL), brine then dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as an oil. Yield 5.3 g.

後処理

  1. customthe cooling bath was removed
  2. waitAfter a further 0.5 h
  3. customthe reaction was quenched with water
  4. additionEthyl acetate (300 mL) was added
  5. washthe reaction mixture washed with water (3×150 mL), 2M HCl (2×50 mL), water (2×50 mL), brine
  6. dry with materialthen dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-e3b7cb78208e441492fc35e6b4e5c1aa
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

関連ノート

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