Tetrahydrofuran → morpholine 5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide

HRID 1463925

반응식

HRID 1463925 반응식
[C:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].C(O[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C#C.[O:38]1CC[CH2:40][CH2:39]1>O>[NH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:31]([O:30][C:24]1[CH:23]=[CH:28][CH:27]=[CH:26][C:25]=1[C:29]#[C:40][C:39](=[O:38])[CH2:2][C:1]([NH2:4])=[O:3])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 155434-AcetylmorpholineHCID 2724682Lithium diisopropylamideHCID 54058410Methyl-2-benzyloxyphenyl propiolate

생성물 1

HCID 86747286morpholine 5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide수율 61%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

Acetyl morpholine (546 ul, 4.72 mmole) was dissolved in 10 ml dry tetrahydrofuran in an oven dried 50 ml two neck round bottom flask under nitrogen. The solution was cooled to 0° C. and was treated slowly dropwise with lithium diisopropylamide (3.2 ml, 4.72 mmole). The mixture was stirred 30 minutes at 0° C. and was treated with methyl-2-benzyloxyphenyl propiolate (600 mg, 2.25 mmole) in 2 ml dry tetrahydrofuran. The reaction mixture was stirred for 1 hour at 0° C. and was diluted with 10 ml water. The volatiles were removed in vacuo and the residue was crystallized from diethyl ether/methanol (20:1). The tan solid was collected, was washed with diethyl ether, and was dried to afford 500 mg (61%) of morpholine-5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide as a tan solid. Melting Point: 224°-227° C.

후처리

  1. dry with materialdried 50 ml two neck round bottom flask under nitrogen
  2. stirringThe reaction mixture was stirred for 1 hour at 0° C.
  3. customThe volatiles were removed in vacuo
  4. customthe residue was crystallized from diethyl ether/methanol (20:1)
  5. customThe tan solid was collected
  6. washwas washed with diethyl ether
  7. customwas dried

출처 및 근거

ORD 기록
ord-c351075d065040a1ba1d312e4d965ae0
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05302613

연결된 노트

불러오는 중…