Triphenylphosphine → 6-(3-Fluoropropoxy)-indan-1-one

HRID 1965065Notes

Reaction equation

HRID 1965065 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[F:12][CH2:13][CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 680423-Fluoro-1-propanol2×HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 679794716-(3-Fluoropropoxy)-indan-1-oneYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-hydroxy-2,3-dihydro-1H-inden-1-one (3.0 g, 20 mmol) in THF (140 mL) were 3-fluoropropan-1-ol (1.67 mL, 22.3 mmol), triphenylphosphine (7.97 g, 30.4 mmol) and diisopropyl azodicarboxylate (5.98 mL, 30.4 mmol) added. The mixture was stirred at r.t. for two days. More 3-fluoropropanol (0.5 mL) was added and the mixture was heated to 45° C. After 2 h the mixture was concentrated, and the crude product was purified by flash chromatography using 0-20% EtOAc in heptane as eluent, affording 3.42 g (81% yield) of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.12-2.26 (m, 2 H), 2.68-2.76 (m, 2 H), 3.04-3.12 (m, 2 H), 4.14 (t, 2 H), 4.61 (t, 1 H), 4.70 (t, 1 H), 7.17-7.22 (m, 2 H), 7.38 (d, 1 H); MS (EI) m/z 208 M+.

Workup

  1. additionadded
  2. temperaturethe mixture was heated to 45° C
  3. concentrationAfter 2 h the mixture was concentrated
  4. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-45068757658a4af0bafa3d749e58d415
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

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