Diiodomethane → HCID 21707623, compound

HRID 1979116Notes

Reaction equation

[CH2:1]([Zn]CC)C.ICI.[CH3:9][C:10]1([CH3:22])[C:14]([CH3:15])=[CH:13][CH2:12][CH:11]1[CH2:16][CH:17]1[O:21][CH2:20][CH2:19][O:18]1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC.ClCCCl>[CH3:15][C:14]12[CH2:1][CH:13]1[CH2:12][CH:11]([CH2:16][CH:17]1[O:18][CH2:19][CH2:20][O:21]1)[C:10]2([CH3:22])[CH3:9]

Participants

Conditions

Temperature: 17.5 °C

Procedure

150 ml (0.15 mol) of 1.0 M solution of diethylzinc in hexane was added to 500 ml of 1,2-dichloroethane under nitrogen. After having added 66.0 g (0.23 mol) of diiodomethane, while maintaining the temperature at 15-20° C. (ice bath), the solution was stirred at room temperature for 30 minutes, then 20.0 g (0.10 mol) of 2-(2,2,3-trimethylcyclopent-3-enylmethyl)-[1,3]dioxolane was added dropwise at 25° C. and the stirring continued for three hours. The reaction mixture was treated with 100 ml of 20% aqueous potassium carbonate, the organic layer separated and the aqueous layer extracted with diethyl ether. The combined organic phases were dried (MgSO4) and evaporated in vacuo. 22 g of the crude product was distilled at 95° C./0.1 Torr to give 14.9 g (71% yield) of 2-(1,2,2-trimethylbicyclo[3.1.0]hex-3-ylmethyl)-[1,3]dioxolane used in the next step without further purification

Workup

waitthe stirring continued for three hours
customthe organic layer separated
extractionthe aqueous layer extracted with diethyl ether
dry with materialThe combined organic phases were dried (MgSO4)
customevaporated in vacuo
distillation22 g of the crude product was distilled at 95° C./0.1 Torr

Sources & evidence

ORD record: ord-60baf0e1a2ec4d558b6c4970c76aeba4
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239314B1

Reaction notes

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