3-Fluoro-1-propanol → 6-(3-Fluoropropoxy)-indan-1-one

HRID 1467921Notes

Reaction equation

HRID 1467921 reaction equation
[F:1][C:2](F)(F)[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][C:12]2=[O:15])=[CH:8][CH:7]=1.OC1C=C2C(CCC2=O)=CC=1.FCCCO>>[F:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][C:12]2=[O:15])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 680423-Fluoro-1-propanol2×HCID 70206596-Hydroxy-1-indanoneHCID 679793426-(3,3,3-trifluoropropoxy)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 679794716-(3-Fluoropropoxy)-indan-1-oneYield 94%

Procedure

The title compound (7.90 g, 94% yield) was prepared following the procedure for Intermediate 16, starting from 6-hydroxy-2,3-dihydro-1H-inden-1-one (5.98 g, 40.4 mmol) and 3-fluoropropan-1-ol (3.34 mL, 44.4 mmol). Additional 3-fluoropropan-1-ol (1.0 mL, 13.3 mmol) was added after stirring overnight to drive the reaction to completion. 1H NMR (500 MHz, CDCl3) δ ppm 2.20 (m, 2 H) 2.73 (m, 2 H) 3.08 (m, 2 H) 4.14 (t, 2 H) 4.61 (t, 3 H) 4.70 (t, 1 H) 7.21 (m, 2 H) 7.38 (d, 1 H); MS (ES+) m/z 208 [M+H]+.

Workup

  1. customthe reaction to completion

Sources & evidence

ORD record
ord-4e719eaa3fb44a31a89dbe0d0506cd85
Source dataset
uspto-grants-2015_04
Patent number
US09000182B2

Reaction notes

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