Methyl formate → Methyl 2-(5-chloro-2-phenoxyphenyl)-3-hydroxyacrylate

HRID 1970103

반응식

HRID 1970103 반응식
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:20](OC)=[O:21].CC(C)([O-])C.[K+]>COC(C)(C)C>[CH3:1][O:2][C:3](=[O:19])[C:4]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:20][OH:21]

참가 물질

5

반응물 3

HCID 7865Methyl formateHCID 23665647Potassium tert-butoxideHCID 59800203Methyl 2-(5-chloro-2-phenoxyphenyl)acetate

생성물 1

HCID 66859650Methyl 2-(5-chloro-2-phenoxyphenyl)-3-hydroxyacrylate

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

A solution of (5-chloro-2-phenoxy-phenyl)-acetic acid methyl ester (167 g, 605 mmol) and methyl formate (173 mL, 2.8 mol) in t-butyl methyl ether (1 L) was cooled to −10° C. To this solution was added potassium t-butoxide (115 g, 1.03 mol) portionwise so that the temperature remained below 0° C. After 30 minutes, the reaction was quenched by addition of 4N aqueous hydrochloric acid (400 mL). The organic layer was separated and washed with water (3×350 mL) and saturated brine (350 mL). The organic fractions were combined and concentrated to dryness and used without purification. The product is 90% E as shown by NMR. 1H NMR (400 MHz, CDCl3) 3.6 (s, 3H, E methyl group; Z methyl is at 3.7), 6.8 (d, 1H), 6.9 (m, 2H), 7.0 (t, 1H), 7.2 (m, 3H), 7.3 (m, 2H), 11.8 (d, 1H, E hydroxy proton; Z hydroxy proton is at 4.7).

후처리

  1. customremained below 0° C
  2. customthe reaction was quenched by addition of 4N aqueous hydrochloric acid (400 mL)
  3. customThe organic layer was separated
  4. washwashed with water (3×350 mL) and saturated brine (350 mL)
  5. concentrationconcentrated to dryness
  6. customused without purification

출처 및 근거

ORD 기록
ord-898c27e16c2c46549b57547591925f46
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426610B2

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