Water → 1-{[4-(Difluoromethoxy)phenyl]ethynyl}-3-propylbenzene

HRID 30553

反応式

HRID 30553 の反応式
[F:1][CH:2]([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14](/[CH:18]=N/NS(C3C=CC(C)=CC=3)(=O)=O)[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1.[CH2:32](B(CC)CC)[CH3:33].[OH-].[Na+].O>C1COCC1>[F:31][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:32][CH3:33])[CH:13]=2)=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 962WaterHCID 7357TriethylboraneHCID 14798Sodium HydroxideHCID 59790336N-[(E)-[3-[2-[4-(difluoromethoxy)phenyl]ethynyl]phenyl]methylideneamino]-4-methylbenzenesulfonamide

生成物 1

HCID 574358561-{[4-(Difluoromethoxy)phenyl]ethynyl}-3-propylbenzene収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of N′-[(1E)-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)methylene]-4-methylbenzenesulfonohydrazide (0.67 mg, 1.52 mmol) in THF was treated with triethyl borane (1.0 M in THF, 1.52 mL, 1.52 mmol), stirred for 2 minutes, treated with NaOH (2.5 N, 0.61 mL, 1.52 mmol), refluxed for 2 hours, cooled to room temperature, poured into water and extracted with EtOAc. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel (ISCO) using hexanes/EtOAc (50/1) as the eluting solvents to give 1-{[4-(difluoromethoxy)phenyl]ethynyl}-3-propylbenzene as a clear oil (386 mg, 89% yield), MS m/e (M+H)+ 286; 1H NMR (400 MHz, DMSO-d6) 0.85 (t, J=7.32 Hz, 3H), 1.57 (m, 2H), 2.6 (t, J=7.32 Hz, 2H), 7.2 (m, 3H), 7.35-7.45 (m, 4H), 7.58 (d, J=8.79 Hz, 2H).

後処理

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified on silica gel (ISCO)

出典と根拠

ORDレコード
ord-2afa4f797d6842c69a7d8f1808c9d185
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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