(((2-Methylenecyclohexyl)methoxy)methyl)benzene → 4-((Benzyloxy)methyl)spiro[2.5]octane

HRID 1748173Notes

Reaction equation

HRID 1748173 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:17]1C2(CCC(C(OCC)=O)CC2)C1>>[CH2:10]([O:9][CH2:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]21[CH2:17][CH2:1]2)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 10703955(((2-Methylenecyclohexyl)methoxy)methyl)benzeneHCID 67984131Ethyl spiro[2.5]octane-6-carboxylate

Product 1

HCID 679839844-((Benzyloxy)methyl)spiro[2.5]octane

Procedure

This intermediate was prepared from (((2-methylenecyclohexyl)methoxy)methyl)benzene by using the same protocol as described for ethyl spiro[2.5]octane-6-carboxylate (I-7A). 1H NMR (400 MHz, CDCl3) δ 7.35-7.31 (m, 4H), 7.29 (m, 1H) 4.49 (q, J=12.4 Hz, 2H), 3.52 (t, J=9.2 Hz, 1H), 3.41 (dd, J=9.2, 5.2 Hz, 1H), 1.72-1.67 (m, 1H), 1.49-1.43 (m, 4H), 1.33-1.26 (m, 1H), 0.88-0.85 (m, 1H), 0.37-0.31 (m, 2H), 0.19-0.14 (m, 2H). MS m/z 231.1 (M+1).

Sources & evidence

ORD record
ord-0427a2ad43f94267bec03a0e8b08f24c
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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