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

HRID 1847188Notes

Reaction equation

HRID 1847188 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-dcf14267d9b04056ae0292fc3793b5c1
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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