Hydrochloric Acid → (Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane

HRID 1267317ノート

反応式

HRID 1267317 の反応式
[H-].[Na+].[Br-].[O:4]1[CH2:9][CH2:8][CH2:7][O:6][CH:5]1[CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:31][C:32]1[O:36][C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:34][C:33]=1[CH2:43][CH2:44][O:45][C:46]1[CH:53]=[CH:52][C:49]([CH:50]=O)=[CH:48][CH:47]=1.Cl>CN(C)C=O>[CH3:31][C:32]1[O:36][C:35]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[N:34][C:33]=1[CH2:43][CH2:44][O:45][C:46]1[CH:47]=[CH:48][C:49](/[CH:50]=[CH:11]\[CH2:10][CH:5]2[O:4][CH2:9][CH2:8][CH2:7][O:6]2)=[CH:52][CH:53]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

生成物 1

HCID 11811571(Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane収率 77.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in oil, 0.78 g) was added in limited amounts, at room temperature, to a solution of [2-(1,3-dioxan-2-yl)ethyl]triphenylphosphonium bromide (8.9 g) in N,N-dimethylformamide (100 ml). The mixture was stirred for 30 minutes at the same temperature range, to which was added 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (5.0 g). The mixture was stirred for 15 minutes at room temperature, then for 5 hours at 70° C. The reaction mixture was poured into ice-water, which was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The residue was purified by means of a silica gel column chromatography. From the fractions eluted with hexane-ethyl acetate (3:1), (Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane (5.1 g, 77%) was obtained as an oily product.

後処理

  1. stirringThe mixture was stirred for 15 minutes at room temperature
  2. waitfor 5 hours at 70° C
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe residue was purified by means of a silica gel column chromatography
  7. washFrom the fractions eluted with hexane-ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-471e933fe3244358932ee7f37dee164a
出典データセット
uspto-grants-2003_04
特許番号
US06552058B1

反応ノート

読み込み中…