Sodium hydride → 3-(3-Bromobenzyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one

HRID 2037415ノート

反応式

HRID 2037415 の反応式
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6](=[O:8])[NH:5][CH2:4][CH2:3]1.[H-].[Na+].[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br>C1COCC1>[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][N:5]1[CH2:4][CH2:3][C:2]([CH3:1])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6]1=[O:8]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 534742826-Methyl-6-phenyl-1,3-oxazinan-2-one

生成物 1

HCID 251824193-(3-Bromobenzyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one収率 32%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 6-methyl-6-phenyl-1,3-oxazinan-2-one (500 mg, 2.62 mmol) and NaH (189 mg, 7.86 mmol) in dry THF (10 mL) was stirred for 1 h. A solution of m-bromobenzyl bromide (1.31 g, 5.24 mmol) in dry THF (3 mL) was added. The mixture was stirred overnight at rt. The reaction mixture was quenched water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by preparative TLC to afford 3-(3-bromobenzyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (300 mg, 32%). 1H NMR (CDCl3): 1.60-1.70 (s, 3H), 2.15-2.30 (m, 1H), 2.35-2.48 (m, 1H), 2.79-2.90 (m, 1H), 3.00-3.10 (m, 1H), 4.30-4.40 (m, 1H), 4.50-4.60 (m, 1H), 6.90-7.00 (m, 1H), 7.00-7.10 (m, 1H), 7.20-7.45 (m, 7H).

後処理

  1. customThe reaction mixture was quenched water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by preparative TLC

出典と根拠

ORDレコード
ord-c4c12095ae4d47a99d1836af690e964f
出典データセット
uspto-grants-2013_11
特許番号
US08575156B2

反応ノート

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