Triethylamine → tert-Butyl-{1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-prop-2-ynyloxy}-dimethylsilane

HRID 1749230ノート

反応式

HRID 1749230 の反応式
[Cl:1][C:2]1[C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[S:5][C:6]=1[CH2:7][CH2:8][CH:9]([OH:12])[C:10]#[CH:11].[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[C:18]([Si:21]([O:12][CH:9]([CH2:8][CH2:7][C:6]1[S:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=2[C:2]=1[Cl:1])[C:10]#[CH:11])([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:17]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 219644275-(3-Chloro-benzo[b]thiophen-2-yl)-pent-1-yn-3-ol

生成物 1

HCID 21964439tert-Butyl-{1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-prop-2-ynyloxy}-dimethylsilane収率 73%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of alcohol 18 (2.20 g, 8.78 mmol) in dichloromethane (15 mL) was treated with DMAP (215 mg, 1.8 mmol), TBSCl (1.59 g, 10.5 mmol), and triethylamine (1.8 mL, 13.2 mmol). The reaction was stirred for 24 h and then saturated sodium bicarbonate solution (50 mL) was added. The mixture was extracted with dichloromethane (2×50 mL) and the combined dichloromethane solution dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (4% ethyl acetate/hexane) gave 3.06 g (6.4 mmol, 73%) of the protected alcohol (19).

後処理

  1. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  2. dry with materialthe combined dichloromethane solution dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (4% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-5a7a843f217f41f4b1223f844a18df9e
出典データセット
uspto-grants-2015_10
特許番号
US09156810B2

反応ノート

読み込み中…