HCID 18348362, compound → HCID 18348371, compound

HRID 2268005Notes

Reaction equation

HRID 2268005 reaction equation
[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[C:14]1(=O)[CH2:25]CCCCCCCC=C[CH2:15]1.C([Mg]Br)(C)=C>O1CCCC1>[C:14]([C:1]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)([CH3:25])=[CH2:15]

Participants

5

Reactant 3

HCID 18348362HCID 18348362, compoundHCID 70119724(3E)-3-Cyclododecen-1-oneHCID 178456138HCID 178456138, compound

Product 1

HCID 18348371HCID 18348371, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of mainly E-cyclododec-3-en-1-one (74%) and Z-cyclododec-3-en-1-one (19%) is treated with isopropenylmagnesium bromide in tetrahydrofuran, to form mainly E-1-isopropenylcyclododec-3-en-1-ol. The purified E-1-isopropenylcyclododec-3-en-1-ol is treated with potassium hydride in N,N-dimethylacetamide in the presence of 18-crown-6, that forms a mixture of diastereomeric 2-methyl-4-vinylcyclododecanone and E-2-methylcyclotetradec-5-en-1-one.

Sources & evidence

ORD record
ord-e1dc79443b844bb4b6224dff3ba3cb91
Source dataset
uspto-grants-2001_12
Patent number
US06326349B1

Reaction notes

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