Triisopropylsilyl chloride → HCID 86758594、化合物

HRID 1017677ノート

反応式

HRID 1017677 の反応式
[OH:1][C:2]1([OH:14])[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:3]1.[CH:15](N(C(C)C)CCCC)([CH3:17])[CH3:16].[CH:26]([Si:29](Cl)([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])([CH3:28])[CH3:27]>CN(C)C=O>[CH2:17]([O:14][C:2]1([O:1][Si:29]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:26]([CH3:28])[CH3:27])[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:3]1)[C:15]#[CH:16]

参加物

5

反応物 3

HCID 139400Triisopropylsilyl chlorideHCID 11062646N,N-DiisopropylbutylamineHCID 18403794HCID 18403794、化合物

生成物 1

HCID 86758594HCID 86758594、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-hydroxy-1-(pyrrolidin-1-yl)methyl-3-hydroxybenzene (0.95 g) in dry dimethylformamide (5 ml) was added by syringe, with stirring, diisopropylbutylamine (1.1 ml) followed by triisopropylsilyl chloride (0.97 ml). The reaction mixture was stirred at ambient temperature for 1 hr, ice (10 g) was added and after stirring for 10 mins, the mixture was poured into ice/water and extracted with ethyl acetate. The extract was washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash column chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 0.65 g of product. Additional fractions were collected, concentrated and chromatographed over silica gel. Concentration of the appropriate fractions gave 0.15 g of product. Total yield 0.80 g (50%).

後処理

  1. stirringThe reaction mixture was stirred at ambient temperature for 1 hr
  2. stirringafter stirring for 10 mins
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customchromatographed (silica gel)
  9. washeluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-33e619dc0963441cb3bc327b48e5e7a1
出典データセット
uspto-grants-2002_11
特許番号
US06479495B1

反応ノート

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