Triphenylphosphine → Methyl 3-fluoro-2-formylpyridine-4-carboxylate

HRID 1426286노트

반응식

HRID 1426286 반응식
[O:1]=[O+][O-].[F:4][C:5]1[C:14]([CH:15]=C)=[N:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[F:4][C:5]1[C:14]([CH:15]=[O:1])=[N:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 24823Ozone2회HCID 696727743-Fluoro-2-vinyl-isonicotinic acid methyl ester

생성물 1

HCID 86666496Methyl 3-fluoro-2-formylpyridine-4-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ozone was bubbled through a solution of methyl 3-fluoro-2-vinylisonicotinate (1.4 g, 7.73 mmol, from Step 2) in methylene chloride (100 mL) at −78° C. until the blue color of excess ozone persisted. Nitrogen was bubbled through the solution for 1 minute to purge excess ozone and then triphenylphosphine (3.9 g, 15 mmol) was added and the solution was warmed to room temperature and stirred overnight. The compound was dry loaded onto silica gel. Flash chromatography eluting with 40% ethyl acetate in hexanes afforded product (0.8 g, 57%) as an off-white crystalline solid. 1H NMR (300 MHz, CDCl3): δ 10.27 (s, 1H), 8.73 (d, 1H), 8.01 (dd, 1H), 4.01 (s, 3H).

후처리

  1. customNitrogen was bubbled through the solution for 1 minute
  2. customto purge excess ozone
  3. customThe compound was dry
  4. washFlash chromatography eluting with 40% ethyl acetate in hexanes afforded product (0.8 g, 57%) as an off-white crystalline solid

출처 및 근거

ORD 기록
ord-d70aede932974ef28b9e4567297aed72
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933085B2

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