Hydrochloric Acid → 1-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol

HRID 396123

反応式

HRID 396123 の反応式
[C:1]([Mg]Br)([CH3:3])=[CH2:2].[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:21]=1)[CH:19]=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.Cl>C1COCC1>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:19]([OH:20])[C:1]([CH3:3])=[CH2:2])[CH:21]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 38498355-(Benzyloxy)-2-nitrobenzaldehydeHCID 178456138HCID 178456138、化合物

生成物 1

HCID 230030651-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol収率 48.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

35.9 ml (16.33 mmol) of a 0.5 M isopropenylmagnesium bromide solution in THF are slowly added at −78° C. to a solution of 3.0 g (11.66 mmol) of 5-benzyloxy-2-nitrobenzaldehyde in 50 ml of THF. After addition is complete, the mixture is stirred at −78° C. for 2 h, then treated with 40 ml of water and warmed to room temperature. The mixture is treated with 10 ml of 1 N hydrochloric acid, the aqueous phase is extracted 2× with ethyl acetate, and the combined organic extracts are dried over sodium sulphate and freed from the solvent in vacuo. Purification of the crude product on silica gel (CH2Cl2) affords 1.7 g (48.7%) of 1-[5-(benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol as a yellow oil.

後処理

  1. additionAfter addition
  2. temperaturewarmed to room temperature
  3. extractionthe aqueous phase is extracted 2× with ethyl acetate
  4. dry with materialthe combined organic extracts are dried over sodium sulphate
  5. customPurification of the crude product on silica gel (CH2Cl2)

出典と根拠

ORDレコード
ord-eb354f2a15d44414b896dc3d2e9aa075
出典データセット
uspto-grants-2003_08
特許番号
US06608049B2

関連ノート

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