Iodoethane → 3-Ethyl-1-(t-butyldimethylsilyl)-4-vinyl-2-azetidinone

HRID 67973Notes

Reaction equation

HRID 67973 reaction equation
[O:1]=[C:2]1[N:9]2[CH:4]([CH2:5][CH2:6]OC2(C)C)[CH:3]1[CH:12]([CH3:14])C.[Si:15](N1C(C=C)CC1=O)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].O=C1N2C(CCOC2(C)C)C1.C(I)C>>[CH2:12]([CH:3]1[CH:4]([CH:5]=[CH2:6])[N:9]([Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:2]1=[O:1])[CH3:14]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 12769229HCID 12769229, compoundHCID 130511448-Oxo-2,2-dimethyl-7alpha-isopropyl-3-oxa-1-azabicyclo[4.2.0]octaneHCID 140681691-(t-Butyldimethylsilyl)-4-vinyl-2-azetidinone

Product 1

HCID 151373693-Ethyl-1-(t-butyldimethylsilyl)-4-vinyl-2-azetidinone

Procedure

Following the procedure for the preparation of 8-oxo-2,2-dimethyl-7α-isopropyl-3-oxa-1-azabicyclo[4.2.0]octane (Example 4b, above), except that an equivalent amount of 1-(t-butyl-dimethylsilyl)-4-vinyl-2-azetidinone is substituted for the 8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane of Example 4b and using ethyl iodide instead of isopropyl iodide, the title compound is obtained.

Sources & evidence

ORD record
ord-c1671875d8404073825873ca75ef87e1
Source dataset
uspto-grants-1982_08
Patent number
US04347368

Reaction notes

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