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

HRID 628162ノート

反応式

HRID 628162 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-36fbeaec54a84e119cc721f0a0037a44
出典データセット
uspto-grants-2016_04
特許番号
US09309283B2

反応ノート

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