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

HRID 991489노트

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HRID 991489 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:26]=[CH:25][C:11]([O:12][CH:13]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:14][CH:15]=[CH2:16])=[CH:10][CH:9]=1.C1C[O:30]CC1>CCOCC>[OH:30][CH2:16][CH2:15][CH2:14][CH:13]([C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1)[O:12][C:11]1[CH:25]=[CH:26][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:9][CH:10]=1

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 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}-benzonitrile

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-5 °C

실험 절차

4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile (from step (i) above; 4.6 g; 13 mmol) was dissolved in dry THF (50 mL) under argon and cooled to −5° C. Borane-methylsulfide complex (BH3xSMe2) (3.5 mL of a 2 M solution in ether) was added dropwise at 0 to 5° C. The mixture was stirred at that temperature for 1.5 h. After 4 h at rt, tlc showed that the reaction was complete. The reaction mixture was quenched with 14 mL of H2O and 5 g of NaBO3. The mixture was stirred overnight, the solvent decanted off, and the residue treated with ether and decanted. The combined organic fractions were washed with brine, dried (Na2SO4), and evaporated. The crude product was purified by chromatography on silica (iso-propanol:ethyl acetate:heptane; 5:20:70). Yield: 2.44 g (58%).

후처리

  1. waitAfter 4 h at rt
  2. customThe reaction mixture was quenched with 14 mL of H2O and 5 g of NaBO3
  3. stirringThe mixture was stirred overnight
  4. customthe solvent decanted off
  5. additionthe residue treated with ether
  6. customdecanted
  7. washThe combined organic fractions were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe crude product was purified by chromatography on silica (iso-propanol:ethyl acetate:heptane; 5:20:70)

출처 및 근거

ORD 기록
ord-ae9179b0175c45618723d8240839ed1c
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465481B1

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