Nitrogen → HCID 22905873、化合物

HRID 2257252ノート

反応式

HRID 2257252 の反応式
Br[C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[O:13][CH2:14][CH2:15]Br.N#N.C([Li])CCC.CCCCCC.[NH4+].[Cl-]>O1CCCC1.CCCCCC.CO.CCOCC>[C:9]([C:4]1[C:3]2[O:13][CH2:14][CH2:15][C:2]=2[CH:7]=[CH:6][CH:5]=1)([CH3:12])([CH3:11])[CH3:10]

参加物

8

反応物 5

HCID 947NitrogenHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 22905874HCID 22905874、化合物HCID 178418339Butyllithium

生成物 1

HCID 22905873HCID 22905873、化合物

試薬・触媒・溶媒 2

HCID 21864698Diethyl ether methanol溶媒HCID 21883165Tetrahydrofuran hexane溶媒

実験手順

A cold solution of 1,5-dibromo-2-(2-bromoethoxy)-3-tert-butylbenzene (5.00 g, 12.05 mmol) in tetrahydrofuran/hexane (100 mL/20 mL) is cooled to -95° C. (MeOH/Et2O, liquid N2). A solution of n-butyl lithium in hexane (12 mL, 30.1 mmol) is added dropwise, and the reaction is allowed to stir for 0.5 h between -95° C. and -80° C. After 4 h, the reaction is poured onto saturated NH4Cl, and extracted with ethylacetate. The organic layer is washed twice with H2O and once with brine. The combined organic layers are dried (MgSO4), filtered, and evaporated. The resulting oil is purified by chromatography over SiO2 using hexanes. The resulting oil is distilled at reduced pressure to give 7-tert-butyl-2,3-dihydrobenzo[b]furan as a low melting white solid.

後処理

  1. waitAfter 4 h
  2. extractionextracted with ethylacetate
  3. washThe organic layer is washed twice with H2O and once with brine
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting oil is purified by chromatography over SiO2
  8. distillationThe resulting oil is distilled at reduced pressure

出典と根拠

ORDレコード
ord-a9f000b2544742d28babbda48987e172
出典データセット
uspto-grants-1997_08
特許番号
US05656661

反応ノート

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