Sodium Iodide → HCID 54368050, compound

HRID 1460725Notes

Reaction equation

[N+:1](=[C:3]([C:14]([CH3:16])=[O:15])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])=[N-:2].C(N(CC)CC)C.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].[I-].[Na+]>C(#N)C.C(Cl)Cl>[N+:1](=[C:3]([C:14]([O:15][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[CH2:16])[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:5])=[N-:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To 1.5 ml of dry acetonitrile were added 83 mg (0.380 millimole) of benzyl 2-diazoacetoacetate, 130 μl (0.933 millimole) of triethylamine and 140 mg (0.929 millimole) of tert-butyldimethylsilyl chloride. A solution obtained by dissolving 70 mg (0.467 millimole) of sodium iodide in 0.5 ml of dry acetonitrile was added dropwise thereto at a room temperature. After the conclusion of the dropwise addition, the reaction mixture was further agitated at 40° C. for 4 hours. To the reaction mixture was added 30 ml of methylene chloride, and the resultant was washed twice with 10 ml portions of water. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to give 118 mg (yield 93.7 %) of the desired compound in a yellow solid. 1H NMR (90 MHz, CDCl3) 4 (ppm): 0.28 (6H, s), 0.97 (9H, s), 4.24 (1H, d), 5.03 (1H, d), 5.21 (2H, s), 7.31 (5H, s).

Workup

customA solution obtained
additionwas added dropwise
customat a room temperature
additionAfter the conclusion of the dropwise addition
washthe resultant was washed twice with 10 ml portions of water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record: ord-eaa1da52e405483c950260570857d397
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071966

Reaction notes

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