Allyl bromide → Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate

HRID 1182799노트

반응식

HRID 1182799 반응식
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[C:9]([CH:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>C(#N)C>[CH2:27]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[C:9]([CH:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH:26]=[CH2:25]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 58236463Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate

생성물 1

HCID 58236458Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate수율 97.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (995 mg, 3.92 mmol) and anhydrous potassium carbonate (650 mg, 4.71 mmol) in acetonitrile (25 ml) was treated with allyl bromide (0.356 ml, 4.11 mmol) and the mixture was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo, water (30 ml) was added and the organic material was extracted with dichloromethane (2×30 ml). The combined organic extracts were evaporated to dryness in vacuo to afford methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate (1125 mg, 97%) as pale yellow oil. 1H NMR (DMSO-d6) 7.58 (1H, s), 6.78 (1H, s), 6.03 (1H, m), 5.52 (1H, dm), 5.33 (2H, s), 5.28 (1H, dm), 4.61 (2H, m), 3.78 (3H, s), 3.42 (3H, s), 3.19 (1H, m), 1.18 (6H, d). MS: [M+Na]+ 317.

후처리

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo, water (30 ml)
  3. additionwas added
  4. extractionthe organic material was extracted with dichloromethane (2×30 ml)
  5. customThe combined organic extracts were evaporated to dryness in vacuo

출처 및 근거

ORD 기록
ord-ba3561fd5e454a37954ac0ad0b083ed5
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664218B2

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