Phosphonium, [2-(1,3-dioxolan-2-yl)ethyl]triphenyl-, bromide (1:1) → Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)ethylidene]azetidine-1-carboxylate

HRID 1717618Notes

Reaction equation

HRID 1717618 reaction equation
CC(C)([O-])C.[K+].[Br-].[O:8]1[CH2:12][CH2:11][O:10][CH:9]1[CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:35]1[CH2:38][N:37]([C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[CH2:36]1>CCOCC>[O:10]1[CH2:11][CH2:12][O:8][CH:9]1[CH2:13][CH:14]=[C:35]1[CH2:36][N:37]([C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[CH2:38]1

Participants

5

Reactant 3

HCID 2733834Phosphonium, [2-(1,3-dioxolan-2-yl)ethyl]triphenyl-, bromide (1:1)HCID 10632047Benzyl 3-oxoazetidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67051614Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)ethylidene]azetidine-1-carboxylateYield 15.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
35 °C

Procedure

Potassium tert-butoxide (1.393 g, 12.4 mmol) and [2-(1,3-dioxolan-2-yl)ethyl]-triphenylphosphonium bromide (5.51 g, 12.4 mmol) were stirred in ether (30 mL) at ambient for 1 h. Phenylmethyl 3-oxoazetidine-1-carboxylate (1.025 g, 5.0 mmol), prepared using procedures similar to those described in Reference 3, was added and the mixture was stirred at 35° C. for 6 h and then at ambient for 4 days. Mixture was filtered through celite and the solid was washed with ether. The filtrate was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, 20% ether in hexanes) gave phenylmethyl 3-[2-(1,3-dioxolan-2-yl)ethylidene]azetidine-1-carboxylate (220 mg, 0.761 mmol, 15% yield): 1H NMR (400 MHz, CDCl3): 7.39-7.28 (m, 5H), 5.43-5.35 (m, 1H), 5.11 (s, 2H), 4.89 (t, 1H), 4.56 (br d, 4H), 4.00-3.92 (m, 2H), 3.91-3.83 (m, 2H), 2.27 (br t, 2H).

Workup

  1. additionwas added
  2. waitat ambient for 4 days
  3. filtrationMixture was filtered through celite
  4. washthe solid was washed with ether
  5. washThe filtrate was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-168782df2bd24662be3c1338992df051
Source dataset
uspto-grants-2010_09
Patent number
US07803839B2

Reaction notes

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