Hexane → Ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoate

HRID 1584338

반응식

HRID 1584338 반응식
[Br-].[CH2:2]([O:4][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH3:3].[CH3:31]CCCCC.C([Li])CCC.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][C:51]=1[O:52][CH2:53][C:54]1[N:55]=[C:56]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[O:57][C:58]=1[CH3:59])C=O>O1CCCC1.O>[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH2:31][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH:49]=[CH:50][C:51]=1[O:52][CH2:53][C:54]1[N:55]=[C:56]([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[O:57][C:58]=1[CH3:59]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 10345271(5-Ethoxycarbonylpentyl)triphenylphosphonium bromideHCID 108297433-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 21224419Ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoate수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of (5-ethoxycarbonylpentyl)triphenylphosphonium bromide (3.0 g) in tetrahydrofuran (THF) (70 ml) was added dropwise, in nitrogen streams at -30° C., a hexane solution of n-butyl lithium (1.6M, 3.9 ml). The mixture was stirred for 30 minutes at the same temperature, to which was added dropwise at -30° C. a solution of 3-methoxy-4-[5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (1.0 g) in tetrahydrofuran (THF) (10 ml). The mixture was stirred for 4 hours at temperature ranging from 50 to 60° C. The reaction mixture was then poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:4), was obtained ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoate (9.7 g, 85%) as an oily product.

후처리

  1. additionwas added dropwise, in nitrogen streams at -30° C.
  2. stirringThe mixture was stirred for 4 hours at temperature
  3. customranging from 50 to 60° C
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationby distilling off the solvent under reduced pressure
  8. washFrom the fraction eluted with ethyl acetate-hexane (1:4)

출처 및 근거

ORD 기록
ord-2c8c9a3a63424b8f92e3be6d51f1ccfe
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932601

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