Water → HCID 70160899, 화합물

HRID 1018374

반응식

HRID 1018374 반응식
[H-].[Na+].[Br-].[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=1)[CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7].[C:34]12([CH2:44][CH2:45][C:46]3[N:50]([CH3:51])[C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=4[CH3:58])=[N:48][C:47]=3[CH:59]=O)[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]3)[CH2:35]1)[CH2:41]2.O>C1COCC1.C(OCC)(=O)C>[CH3:4][O:5][C:6](=[O:7])[C:8]1[CH:33]=[CH:32][CH:31]=[C:10]([CH:11]=[CH:59][C:47]2[N:48]=[C:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[CH3:58])[N:50]([CH3:51])[C:46]=2[CH2:45][CH2:44][C:34]23[CH2:43][CH:38]4[CH2:37][CH:36]([CH2:42][CH:40]([CH2:39]4)[CH2:41]2)[CH2:35]3)[CH:9]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromideHCID 184054185-(2-Adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbaldehyde

생성물 1

HCID 70160899HCID 70160899, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (60% dispersion in oil) (122 mg, 3.05 mmol) was added to an ice cooled suspension of 3-methoxycarbonyl-benzyl-triphenylphosphonium bromide (1.25 g, 2.54 mmol) in THF (5 ml). The yellow suspension was stirred at room temperature for 10 min, cooled to 0° C. and the solution of the product of step b (7686 mg, 2.12 mmol) in THF (5 ml) was added. The suspension was allowed to warm to room temperature and stirred for 72 h. Water (2 ml), then ethyl acetate (40 ml) were added. The organic phase was washed with water (30 ml), brine (30 ml), dried (MgSO4) and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, hexane/ethyl acetate 5:2) to afford the product as 2:1 mixture of trans/cis isomers (778 mg, 74%).

후처리

  1. temperaturecooled
  2. temperaturecooled to 0° C.
  3. temperatureto warm to room temperature
  4. stirringstirred for 72 h
  5. washThe organic phase was washed with water (30 ml), brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated
  8. customThe crude product was purified by flash column chromatography (silica, hexane/ethyl acetate 5:2)
  9. customto afford the product
  10. additionas 2:1 mixture of trans/cis isomers (778 mg, 74%)

출처 및 근거

ORD 기록
ord-67e3a5df10fa4d52a1bf856fb10494f4
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479531B1

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