Methyl Acrylate → 6'-(3-Fluoropropoxy)-4-hydroxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one

HRID 1467922Notes

Reaction equation

HRID 1467922 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][C:11]3([CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[C:12]2=[O:15])=[CH:8][CH:7]=1.FCCCOC1C=C2C(CCC2=O)=CC=1.C(OC)(=O)C=C>>[F:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][C:11]3([CH2:16][CH2:17][CH:18]([OH:21])[CH2:19][CH2:20]3)[C:12]2=[O:15])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 679793976'-(3,3,3-Trifluoropropoxy)spiro[cyclohexane-1,2'-indene]-1',4(3'H)-dioneHCID 679794716-(3-Fluoropropoxy)-indan-1-one2×

Product 1

HCID 679796486'-(3-Fluoropropoxy)-4-hydroxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one

Procedure

The title compound was prepared following the method described for Intermediate 17 and in a subsequent step the method described for Intermediate 18, starting from 6-(3-fluoropropoxy)-2,3-dihydro-1H-inden-1-one (Intermediate 20, 3.16 g, 15.2 mmol) and methyl acrylate (3.01 mL, 33.4 mmol). The product was purified by flash chromatography (0-100% EtOAc in heptane) to afford the title compound as a 2:1 mixture of diastereomers (0.910 g, 32% yield). 1H NMR (500 MHz, CDCl3) δ ppm 1.43-1.52 (m, 3 H) 1.74-1.85 (m, 2 H) 1.95 (td, 1 H) 2.14-2.24 (m, 2 H) 2.93-3.02 (m, 2 H) 3.73-3.80 (m, 1 H) 4.10-4.16 (m, 2 H) 4.61 (t, 1 H) 4.70 (t, 1 H) 7.18-7.22 (m, 2 H) 7.31-7.38 (m, 1 H); MS (ES+) m/z 293.09 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customThe product was purified by flash chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-e50ee7e37c074ec9b105e2331f74a799
Source dataset
uspto-grants-2015_04
Patent number
US09000182B2

Reaction notes

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