Hydrochloric Acid → Diethyl 2-(difluoromethyl)-4-ethyl-6-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 1111072ノート

反応式

HRID 1111072 の反応式
[F:1][C:2]([F:26])([F:25])[C:3]1[NH:4][C:5]([C:21](F)([F:23])[F:22])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]([CH2:14][CH3:15])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].N12CCCNC1C=CCCC2.Cl>O1CCCC1>[F:23][CH:21]([F:22])[C:5]1[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([CH2:14][CH3:15])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:3]([C:2]([F:26])([F:1])[F:25])[N:4]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 139576211,4-Dihydro-2,6-bis(trifluoromethyl)-4-ethylpyridine-3,5-dicarboxylic acid diethyl esterHCID 150726561,2,3,4,6,7,8,10A-octahydropyrimido[1,2-a]azepine

生成物 1

HCID 13957657Diethyl 2-(difluoromethyl)-4-ethyl-6-(trifluoromethyl)-3,5-pyridinedicarboxylate収率 78.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 1558 g (4.00 moles) of diethyl 2,6-bis(trifluoromethyl)-l,4-dihydro-4-ethyl-3,5-pyridinedicarboxylate, 628 g (4.0 moles) of 1,8-diazabicyclo-[5.4.0]-undec-5-ene (DBU), and 500 ml of tetrahydrofuran is held at reflux for 19 hours, cooled and poured into a mixture of 2 kg of ice and 250 ml of concentrated hydrochloric acid. The organic layer is separated and the aqueous layer extracted with 500 ml of CH2Cl2 twice. The combined organic materials are dried (MgSO4) and concentrated. The residue is kugelrohr distilled at 1 torr (pot temperature of 150°-160 ° C.) to give 1158 g (78.5%) of desired product, nD25 1.4458.

後処理

  1. temperatureat reflux for 19 hours
  2. temperaturecooled
  3. customThe organic layer is separated
  4. extractionthe aqueous layer extracted with 500 ml of CH2Cl2 twice
  5. dry with materialThe combined organic materials are dried (MgSO4)
  6. concentrationconcentrated
  7. distillationThe residue is kugelrohr distilled at 1 torr (pot temperature of 150°-160 ° C.)

出典と根拠

ORDレコード
ord-db5cc8ae637640d4bc5e52d5c8cbf950
出典データセット
uspto-grants-1990_12
特許番号
US04978384

反応ノート

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