Lithium Hexamethyldisilazide → 1-[3-Tert-butyl-5-(3-hydroxypropoxy)phenyl]ethanone

HRID 1524561ノート

反応式

HRID 1524561 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21]C2CCCCO2)[CH:16]=1)[C:8](N(OC)C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:28][Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Mg]Br>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([C:8](=[O:9])[CH3:28])[CH:14]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][OH:21])[CH:16]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 2733832Lithium HexamethyldisilazideHCID 581369583-tert-Butyl-N-methoxy-N-methyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 669361201-[3-Tert-butyl-5-(3-hydroxypropoxy)phenyl]ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-tert-Butyl-N-methoxy-N-methyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzamide (O3.059; 5.49 g) was dissolved in THF (100 ml), cooled to 0° C. and admixed with lithium bis(trimethylsilyl)amide (14.47 ml, 1 M in MTB ether). After stirring at 0° C. for 30 min, methylmagnesium bromide (9.65 ml, 3 M in ether) was added dropwise. The cooling bath was removed and, after stirring at RT for 2 h, the mixture was diluted with water and extracted by shaking with EA. The EA phase was dried over magnesium sulfate, filtered and concentrated by rotary evaporation. The residue was purified using silica gel (200 g, n-heptane/EA 4:1). 3.4 g of the title compound were obtained.

後処理

  1. customThe cooling bath was removed
  2. stirringafter stirring at RT for 2 h
  3. additionthe mixture was diluted with water
  4. extractionextracted
  5. stirringby shaking with EA
  6. dry with materialThe EA phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified

出典と根拠

ORDレコード
ord-2945d61f72ae4af9b31fb1e969394a72
出典データセット
uspto-grants-2015_07
特許番号
US09079906B2

反応ノート

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