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

HRID 63081

反応式

HRID 63081 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-77ac05f634da4031a9aa6f68c6b0934e
出典データセット
uspto-grants-2016_09
特許番号
US09447045B2

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