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

HRID 396123

반응식

HRID 396123 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 38498355-(Benzyloxy)-2-nitrobenzaldehydeHCID 178456138HCID 178456138, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-eb354f2a15d44414b896dc3d2e9aa075
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608049B2

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