Water → 4-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

HRID 411538노트

반응식

HRID 411538 반응식
B.CSC.[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][C:12]1[CH:30]=[CH:29][C:15]([O:16][CH:17]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[CH2:18][CH:19]=[CH2:20])=[CH:14][CH:13]=1.O.CC[O:34]CC>C1COCC1>[OH:34][CH2:20][CH2:19][CH2:18][CH:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=1)[O:16][C:15]1[CH:29]=[CH:30][C:12]([O:11][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:5]2)=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 12423031(Dimethyl sulfide)trihydroboronHCID 222356714-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile

생성물 1

HCID 222354084-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Borane-dimethylsulfide complex (3.5 mL of 2 M in ether, 7 mmol) was added dropwise to a cooled (5° C.) solution of 4-{1-[4-(tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile (see step (i) above; 4.6 g, 13 mmol) in dry THF over a period of 15 min. The resulting mixture was stirred at between 0 and 5° C. for 1.5 h. Stirring was then continued for a further 4 h at rt. Water (14 mL) and NaBO3 (5 g) were added and the mixture stirred overnight. Ether was added and the resulting organic layer was separated, washed with water and brine, dried and then evaporated. The resulting residue was purified by chromatography on silica gel, eluting with IPA:EtOAc:heptane (5:20:70), to give 2.44 g (58%) of the sub-title compound.

후처리

  1. stirringStirring
  2. waitwas then continued for a further 4 h at rt
  3. stirringthe mixture stirred overnight
  4. customthe resulting organic layer was separated
  5. washwashed with water and brine
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified by chromatography on silica gel
  9. washeluting with IPA:EtOAc:heptane (5:20:70)

출처 및 근거

ORD 기록
ord-a7c7ce7d0bff421ebc4c7b1491249170
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559162B2

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