Triphenylphosphine → 6-(3,3,3-trifluoropropoxy)-2,3-dihydro-1H-inden-1-one

HRID 539291Notes

Reaction equation

HRID 539291 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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:31][C:32]([F:37])([F:36])[CH2:33][CH2:34]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:31][C:32]([F:37])([F:36])[CH2:33][CH2:34][O: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

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1375123,3,3-Trifluoro-1-propanol2×HCID 70206596-Hydroxy-1-indanone

Product 1

HCID 679793426-(3,3,3-trifluoropropoxy)-2,3-dihydro-1H-inden-1-oneYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-hydroxy-2,3-dihydro-1H-inden-1-one (3.0 g, 20.3 mmol) in THF (140 mL) were triphenylphosphine (7.97 g, 30.4 mmol) and 3,3,3-trifluoropropan-1-ol (1.963 mL, 22.27 mmol) added. Diisopropyl azodicarboxylate (5.98 mL, 30.4 mmol) was added dropwise and the mixture was left stirring at r.t. overnight. Since there was starting material remaining, 3,3,3-trifluoro-1-propanol (0.892 mL, 10.1 mmol) was added dropwise and stirring was continued. After 30 min the mixture was heated to 40° C. and after 1 h the mixture was concentrated. The crude product was purified by flash chromatography (0-12% EtOAc in heptane as eluent) to afford 1.08 g (22% yield) of the title compound (containing some diisopropyl azodicarboxylate): 1H NMR (500 MHz, CDCl3) δ 2.65 (qt, 2 H), 2.71-2.77 (m, 2 H), 3.05-3.13 (m, 2 H), 4.23 (t, 2 H), 7.17-7.23 (m, 2 H), 7.40 (d, 1 H); MS (ES+) m/z 245 [M+H]+.

Workup

  1. additionadded
  2. waitthe mixture was left
  3. stirringstirring
  4. temperatureAfter 30 min the mixture was heated to 40° C. and after 1 h the mixture
  5. concentrationwas concentrated
  6. customThe crude product was purified by flash chromatography (0-12% EtOAc in heptane as eluent)

Sources & evidence

ORD record
ord-b290a7c6aa144ae093962c5ab62f6233
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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