4-Hydroxybenzyl Alcohol → Ethyl 2-(3,5-dimethylphenoxy)acetate

HRID 630628노트

반응식

HRID 630628 반응식
[C:1](O)(=O)[CH2:2][CH2:3]C#C.O[CH2:9]C1C=CC(O)=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33].[CH2:38]1[CH2:42][O:41][CH2:40][CH2:39]1>>[CH3:3][C:2]1[CH:1]=[C:42]([CH:38]=[C:39]([CH3:9])[CH:40]=1)[O:41][CH2:33][C:32]([O:35][CH2:36][CH3:37])=[O:34]

참가 물질

6

반응물 5

HCID 1254-Hydroxybenzyl AlcoholHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acid

생성물 1

HCID 7018365Ethyl 2-(3,5-dimethylphenoxy)acetate수율 40%

실험 절차

Referring to FIG. 42, a mixture of pent-4-ynoic acid (1.10 g. 11.2 mmol), 4-(hydroxymethyl)phenol (1.40 g, 11.2 mmol) and DCC (3.5 g, 16.8 mmol) in THF (30 mL) was stirred at room temperature overnight. Ethyl acetate was added to dilute the mixture and the white solid was filtered off. The filtrate was collected and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=3:1 to 2:1) to afford compound 1 (0.91 g, 40% yield); 1H NMR (300 MHz, DMSO-d6): δ 7.35 (d, J=8.4 Hz, 2H), 7.06 (d, J=8.4 Hz, 2H), 5.23 (t, J=6.0 Hz, 1H), 4.49 (d, J=5.7 Hz, 2H), 2.90-2.89 (m, 1H), 2.81-2.76 (m, 2H), 2.55-2.50 (m, 2H).

후처리

  1. additionto dilute the mixture
  2. filtrationthe white solid was filtered off
  3. customThe filtrate was collected
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=3:1 to 2:1)

출처 및 근거

ORD 기록
ord-a1f6782e27954fb280d4e741b02bccf1
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315542B2

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