Sodium Azide → cis-2-Azido-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene

HRID 370014ノート

反応式

HRID 370014 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@H:8](OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:7][CH2:6]2.[N-:30]=[N+:31]=[N-:32].[Na+].C1OCCOCCOCCOCCOC1>CN(C)C=O>[N:30]([C@H:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C@H:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N+:31]=[N-:32]

参加物

5

反応物 3

HCID 33557Sodium AzideHCID 3633615-Crown-5HCID 54035226trans-6-Methoxy-1-phenyl-2-(4-methylbenzenesulfonyl)oxy-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 53966566cis-2-Azido-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene収率 62%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A N,N-dimethylformamide solution (50 mL) of crude trans-6-methoxy-1-phenyl-2-(4-methylbenzenesulfonyl)oxy-1,2,3,4-tetrahydronaphthalene 30 (3.4 g), sodium azide (3.78 g, 58.3 mmol) and 15-crown-5 (6.61 mL, 33.2 mmol) was heated at 75° C. for 7 h. The reaction mixture was poured into ice water (200 mL), and the product was extracted into diethyl ether (3×50 mL). The organic extracts were combined and washed successively with water (4×100 mL) and a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. The solvent was evaporated in vacuo, and the remaining residue was purified by medium pressure chromatography using 3% ethyl acetate in hexanes as the eluent to give crude cis-2-azido-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene 31 (1.35 g, ~62%) as an oil which was used without further purification in the subsequent step.

後処理

  1. extractionthe product was extracted into diethyl ether (3×50 mL)
  2. washwashed successively with water (4×100 mL)
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe remaining residue was purified by medium pressure chromatography

出典と根拠

ORDレコード
ord-9079d54aad694bd095f09c2d4107f75e
出典データセット
uspto-grants-2000_10
特許番号
US06140354

反応ノート

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