Methyl Acrylate → 6'-Isobutoxyspiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione

HRID 1770916

Reaction equation

HRID 1770916 reaction equation
F[CH2:2][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.[CH2:22](OC1C=C2C(CCC2=O)=CC=1)C(C)C.C(OC)(=O)C=C>>[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)[CH:3]([CH3:22])[CH3:2]

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 440728476-Isobutoxyindan-1-one2×HCID 679795576'-(3-Fluoropropoxy)spiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione

Product 1

HCID 679793196'-Isobutoxyspiro[cyclohexane-1,2'-indene]-1',4(3'H)-dioneYield 72%

Procedure

The title compound (3.02 g, 72% yield) was prepared using the method described for Intermediate 63 starting from 6-isobutoxy-2,3-dihydro-1H-inden-1-one (Intermediate 66, 3.0 g, 14.7 mmol) and methyl acrylate (2.92 mL, 32.3 mmol): 1H NMR (400 MHz, CDCl3) δ ppm 1.04 (m, 8H) 1.86 (m, 2H) 2.11 (dt, 1H) 2.21 (m, 2H) 2.47 (m, 3H) 2.70 (m, 2H) 3.15 (s, 2H) 3.76 (m, 3H) 7.20 (m, 1H) 7.25 (m, 1H) 7.38 (d, 1H); MS (ES+) m/z 287 [M+H]+.

Sources & evidence

ORD record
ord-df894d5eff98437c9550230720db36b7
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Linked notes

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