Triphenylphosphine → 6-[(3,3-Difluorocyclobutyl)methoxy]-2,3-dihydro-1H-inden-1-one

HRID 1468069Notes

Reaction equation

HRID 1468069 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][C:13]1([F:19])[CH2:16][CH:15]([CH2:17]O)[CH2:14]1.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][C:13]1([F:19])[CH2:16][CH:15]([CH2:17][O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C:8]3=[O:11])=[CH:4][CH:3]=2)[CH2:14]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70206596-Hydroxy-1-indanoneHCID 45480377(3,3-Difluorocyclobutyl)methanol

Product 1

HCID 867067186-[(3,3-Difluorocyclobutyl)methoxy]-2,3-dihydro-1H-inden-1-oneYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-hydroxy-2,3-dihydro-1H-inden-1-one (3.6 g, 24.3 mmol) in THF (60 mL) were (3,3-difluorocyclobutyl)methanol (2.97 g, 24.3 mmol) and triphenylphosphine (9.56 g, 36.45 mmol) added. Diisopropyl azodicarboxylate (7.18 mL, 36.5 mmol) was added dropwise. The reaction mixture was stirred at r.t. overnight. The material was purified by flash column chromatography using a gradient of 0-100% EtOAc in heptane, providing 3.67 g (60% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) ppm 2.30 (br. s., 1H) 2.42-2.52 (m, 6H) 2.54-2.62 (m, 1H) 2.63-2.66 (m, 2H) 2.67-2.76 (m, 2H) 2.98-3.04 (m, 2H) 4.08 (d, 2H) 7.10 (d, 1H) 7.26 (dd, 1H) 7.48 (d, 1H); MS (ES+) m/z 253 [M+H]+.

Workup

  1. additionadded
  2. customThe material was purified by flash column chromatography

Sources & evidence

ORD record
ord-acb985c483774953a2b2e29df3e02d41
Source dataset
uspto-grants-2015_04
Patent number
US09000185B2

Reaction notes

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