Cyclobutylcarbinol → HCID 67979411, compound

HRID 1468073Notes

Reaction equation

HRID 1468073 reaction equation
F[C:2]1(F)[CH2:5][CH:4]([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][CH2:13][C:14]3=[O:17])=[CH:10][CH:9]=2)[CH2:3]1.[OH:19][C:20]1[CH:28]=[C:27]2C(CCC2=O)=[CH:22][CH:21]=1.C1(CO)CCC1>>[CH:4]1([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][C:13]4([CH2:27][CH2:28][C:20](=[O:19])[CH2:21][CH2:22]4)[C:14]3=[O:17])=[CH:10][CH:9]=2)[CH2:5][CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 78130CyclobutylcarbinolHCID 70206596-Hydroxy-1-indanoneHCID 867067186-[(3,3-Difluorocyclobutyl)methoxy]-2,3-dihydro-1H-inden-1-one

Product 1

HCID 67979411HCID 67979411, compoundYield 58%

Conditions

Temperature
45 °C

Procedure

The title compound (2.56 g, 58% yield) was prepared using the procedure described for Intermediate 11, starting from 6-hydroxy-2,3-dihydro-1H-inden-1-one (3.0 g, 20.3 mmol) and cyclobutylmethanol (2.10 mL, 22.3 mmol). The mixture was heated to 45° C. and left stirring over a weekend. 1H NMR (500 MHz, CDCl3) δ ppm 1.81-2.03 (m, 4H), 2.11-2.20 (m, 2H), 2.69-2.74 (m, 2H), 2.78 (dt, 1H), 3.04-3.12 (m, 2H), 3.96 (d, 2H), 7.17-7.22 (m, 2H), 7.36 (d, 1H); MS (ES+) m/z 217 [M+H]+.

Workup

  1. waitleft

Sources & evidence

ORD record
ord-75cfafbceb7844fabe6b2784b24fd1d6
Source dataset
uspto-grants-2015_04
Patent number
US09000185B2

Reaction notes

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