Triphenylphosphine → 6-(3,3,3-trifluoropropoxy)-3,4-dihydronaphthalen-1(2H)-one

HRID 63081

반응식

HRID 63081 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[F:13][C:14]([F:19])([F:18])[CH2:15][CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOC(C)=O>[F:13][C:14]([F:19])([F:18])[CH2:15][CH2:16][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 1375123,3,3-Trifluoro-1-propanolHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 645552426-(3,3,3-trifluoropropoxy)-3,4-dihydronaphthalen-1(2H)-one수율 53%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

6-Hydroxy-1-tetralone (3.5 g, 21.6 mmol), 3,3,3-trifluoro-1-propanol (4.93 g, 43.2 mmol) and triphenylphosphine (11.3 g, 43.2 mmol) were combined in THF (80 mL). DIAD (8.7 g, 43.2 mmol) was added, and the reaction stirred overnight at rt. The solution was diluted with EtOAc (100 mL) and washed with brine. Organics were dried (MgSO4) and concentrated. Purification by silica gel chromatography (10-50% EtOAc/hexanes) gave 2.93 g (53%) of the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 8.02 (d, 1H, J=8.7 Hz), 6.82 (dd, 1H, J=8.7, 2.5 Hz), 6.71 (d, 1H, J=2.4 Hz), 4.25 (t, 2H, J=6.6 Hz), 2.93 (t, 2H, J=6.1 Hz), 2.59-2.71 (m, 4H), 2.08-2.16 (m, 2H). [M+H] calc'd for C13H13F3O2, 259; found 259.

후처리

  1. washwashed with brine
  2. dry with materialOrganics were dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (10-50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-77ac05f634da4031a9aa6f68c6b0934e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447045B2

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