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

HRID 1426286ノート

反応式

HRID 1426286 の反応式
[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]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 24823Ozone2 回HCID 696727743-Fluoro-2-vinyl-isonicotinic acid methyl ester

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d70aede932974ef28b9e4567297aed72
出典データセット
uspto-grants-2015_01
特許番号
US08933085B2

反応ノート

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