Ammonium Chloride → HCID 15117218, compound

HRID 1029614Notes

Reaction equation

[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[CH2:12]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1)=[O:17])[CH:13]=[CH2:14].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH2:12]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C:20]([OH:23])([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:19]1)=[O:17])[CH:13]=[CH2:14]

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of trimethylsilylacetylene (16.3 ml) in tetrahydrofuran (100 ml) were added successively a solution of n-butyllithium in n-hexane (1.50M, 70 ml) and a solution of 1-allyloxycarbonyl-3-oxopyrrolidine (15 g) in tetrahydrofuran (15 ml) at -50° C. After stirring at -50° C. for 1 hour, to the mixture was added a mixture of aqueous ammonium chloride and ethyl acetate at 0° C. The organic layer was separated and the aqueous layer was extracted with ethyl acetate twice. The organic layers were combined washed with 1N hydrochloric acid, water and brine successively and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave 1-allyloxycarbonyl-3-hydroxy-3-trimethylsilylethynylpyrrolidine (19.5 g).

Workup

customat -50° C
additionwas added
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate twice
washThe organic layers were combined washed with 1N hydrochloric acid, water and brine successively
dry with materialdried over magnesium sulfate
customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-620160e0167d45c9a8c8cf1840cfaab8
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102877

Reaction notes

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