Allyl Alcohol → HCID 19605258, compound

HRID 1603638Notes

Reaction equation

HRID 1603638 reaction equation
C(O)C=C.CC(C)([O-])C.[K+].[C:11]([S:14][CH2:15][C:16]1[CH:27]=[CH:26][C:19]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])=[CH:18][CH:17]=1)(=O)[CH3:12].C([O:31][CH:32]1[NH:35]C(=O)C1)(=O)C>O1CCCC1>[CH2:23]([O:22][C:20]([C:19]1[CH:26]=[CH:27][C:16]([CH2:15][S:14][CH:11]2[NH:35][C:32](=[O:31])[CH2:12]2)=[CH:17][CH:18]=1)=[O:21])[CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 1199814-Acetoxy-2-azetidinoneHCID 19605229HCID 19605229, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19605258HCID 19605258, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Allyl alcohol (27 ml) in dry tetrahydrofuran (50 ml) was added dropwise to a solution of potassium tert-butoxide (4.93 g, 0.044 moles) in dry tetrahydrofuran (100 ml). After stirring for 5 minutes a solution of allyl 4-(acetylthiomethyl)benzoate (10.1 g, 0.04 moles) in dry tetrahydrofuran (100 ml) was added dropwise. After stirring for 15 minutes a solution of 4-acetoxyazetidin-2-one (5.16 g, 0.04 moles) was added dropwise. The mixture was stirred for 1 hour and evaporated. The residue was partitioned between ethyl acetate and water and the aqueous was extracted with ethyl acetate. The combined extracts were washed with brine, dried and evaporated. Flash chromatography (silica gel, ethyl acetate-petrol) gave 4-(4-Allyloxycarbonylbenzylthio)azetidin-2-one as an oil (9.1 g, 82% yield. 1H NMR δ (CDCl3) 2.84 (1H, dd, H3a), 4.31 (1H, dd, H3b), 3.88 (2H, s, S--CH2), 4.68 (1H, dd, H4), 4.78 (2H, m, CH2O), 5.35 (2H, m, CH2CH--), 6.05 (1H, m, CHCH2), 6.07 (1H, br. singlet, N--H), 7.40 (2H, d, Ph-H), 8.03 (2H, d, Ph-H).

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. extractionthe aqueous was extracted with ethyl acetate
  6. washThe combined extracts were washed with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-d098b6890652424b9c0b1bad379ad3f7
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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