Acetic Acid → t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate

HRID 1107175노트

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HRID 1107175 반응식
C([O:9][CH2:10]/[C:11](/[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[OH:9][CH2:10]/[C:11](=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)/[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 69907940(E)-2-t-Butoxycarbonyl-7-phenylhept-2-enyl benzoate

생성물 1

HCID 86755388t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate수율 51%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

(E)-2-t-Butoxycarbonyl-7-phenylhept-2-enyl benzoate (5.9 g, 15 mmol) is dissolved in MeOH (75 mL) and cooled to 0° C. K2CO3 (2 g, 15 mmol) is added with stirring and the reaction is allowed to warm to 23° C. After 2 hours the reaction is neutralized with HOAc and the reaction is concentrated to approximately half of its volume. After diluting with ether (500 mL), the solution is washed with water (50 mL) and brine (50 mL). The resulting solution is dried (MgSO4) and concentrated in vacuo. The crude reaction mixture is purified by column chromatography (silica, 25% ether in petroleum ether) to give t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate (2.2 g, 51%): 1H NMR (300 MHz, CDCl3) δ 7.30-7.25 (m, 2H), 7.20-7.15 (m, 3H), 6.75 (t, J=7.7 Hz, 1H), 4.28 (d, J=6.8 Hz, 2H), 2.65-2.60 (m, 3H), 2.26 (q, J=7.5 Hz, 2H), 1.71-1.61 (m, 2H), 1.53-1.43 (m, 11H).

후처리

  1. temperatureto warm to 23° C
  2. concentrationthe reaction is concentrated to approximately half of its volume
  3. additionAfter diluting with ether (500 mL)
  4. washthe solution is washed with water (50 mL) and brine (50 mL)
  5. dry with materialThe resulting solution is dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customis purified by column chromatography (silica, 25% ether in petroleum ether)

출처 및 근거

ORD 기록
ord-f7a879bc6a8847aa9e9f30d2f6deb0d2
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057369

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