Oxetane → 2,6,7-Trioxabicyclo(2.2.2)octane, 4-cyclohexyl-1-(4-ethylnylphenyl)-

HRID 622721Notes

Reaction equation

HRID 622721 reaction equation
O1CCC1.[CH:5]1([C:11]2([CH2:15][OH:16])[CH2:14][O:13][CH2:12]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.Br[CH:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)[CH2:19]Br>>[CH:5]1([C:11]23[CH2:12][O:13][C:25]([C:24]4[CH:28]=[CH:29][C:21]([C:18]#[CH:19])=[CH:22][CH:23]=4)([O:16][CH2:15]2)[O:26][CH2:14]3)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 10423OxetaneHCID 1840024-(1,2-dibromoethyl)benzoyl ChlorideHCID 19373305(3-Cyclohexyloxetan-3-yl)methanol

Product 1

HCID 1760872,6,7-Trioxabicyclo(2.2.2)octane, 4-cyclohexyl-1-(4-ethylnylphenyl)-

Procedure

Utilizing Procedure 2, 4-cyclohexyl-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2.2.2]octane was prepared from its respective oxetane. The 3-cyclohexyl-3-hydroxymethyloxetane was reacted with 4-(1,2-dibromoethyl)benzoyl chloride by the method of Procedure 2. The resulting product was characterized by NMR (300 MHz, CDCl3): δ 1.0-1.4 and 1.6-2.0 (11H, m, cyclohexyl CH2), 3.9-4.1 (2H, m, CH2Br), 4.4 (2H, s, CH2O), 4.55 (4H, d of d, CH2OCH2), 5.1 (1H, d of d, ArCHBr), 7.45 (2H, d, aromatic), 8.1 (2H, d, aromatic).

Sources & evidence

ORD record
ord-36eba9e7210646b4bc38ca3444cc9dec
Source dataset
uspto-grants-1988_09
Patent number
US04772624

Reaction notes

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