Sodium hydride → 2-[3-(Methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole

HRID 7713

反応式

HRID 7713 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([CH3:17])=[C:14]([OH:16])[CH:15]=1.[H-].[Na+].Br[CH2:21][O:22][CH2:23]Br>C1COCC1>[CH3:21][O:22][CH2:23][O:16][C:14]1[CH:15]=[C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH:11]=[CH:12][C:13]=1[CH3:17]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 13349653Bromo(bromomethoxy)methaneHCID 219910005-(1,3-Benzoxazol-2-yl)-2-methylphenol

生成物 1

HCID 219910022-[3-(Methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (200 mg, 0.89 mmol) in THF (6 mL) was cooled to −78° C. under Argon and sodium hydride (24 mg, 1.0 mmol) was added. After 30 min at this temperature, bromomethyl ether (225 mg, 1.8 mmol) was added via syringe. The reaction was warmed to rt for 1 h. The reaction mixture was concentrated and the residue was purified by flash column (silica gel, hexanes:EtOAc 4:1) to afford 2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole. MS (ESI) 270 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash column (silica gel, hexanes:EtOAc 4:1)

出典と根拠

ORDレコード
ord-aa5a2b97ad7343c18a3533749cd3c636
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

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