Tetrahydropyranyl ether → HCID 70603942, compound
Reaction equation
OC(CCCCC)/C=C/[CH:5]1[CH2:7][C:6]1([C:12]([O:14][CH3:15])=O)C(OC)=O.O1CCCCC1OC1CCCCO1.[C:34]([O:37][CH2:38][C@@H:39]1[C:41]([C:47]([O:49][CH2:50][CH3:51])=[O:48])([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C@H:40]1[CH:52]=[CH:53][CH:54]([OH:60])[CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])(=[O:36])[CH3:35]>>[C:34]([O:37][CH2:38][C@@H:39]1[C:41]([C:47]([O:49][CH2:50][CH3:51])=[O:48])([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C@H:40]1[CH:52]=[CH:53][CH:54]([O:60][CH:12]1[CH2:6][CH2:7][CH2:5][CH2:15][O:14]1)[CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])(=[O:36])[CH3:35].[CH3:38][C@@H:39]1[C:41]([C:42]([O:44][CH3:45])=[O:43])([C:47]([O:49][CH3:50])=[O:48])[C@H:40]1[CH:52]=[CH:53][CH:54]([OH:60])[CH2:55][CH:56]=[CH:57][CH3:58]Participants
Procedure
In the same manner but using an equivalent amount of one of the compounds of formula II (R5 = H), for example, the compounds listed in Example 43 to 76, instead of dimethyl trans-2-(3-hydroxy-1-octenyl)cyclopropane-1,1-dicarboxylate, then the corresponding tetrahydropyranyl ether compound of formula II (R5 = tetrahydropyranyl) is obtained, for example, the corresponding tetrahydropyranyl ether compounds of Examples 43 to 76, respectively. More specifically exemplified, in the same manner diethyl trans-3-(acetoxymethyl)-2-(3-hydroxy-1-octenyl)cyclopropane-1,1-dicarboxylate (Example 73) gives diethyl trans-3-(acetoxymethyl)-2-{3-[(tetrahydropyran-2-yl)oxy]-1-octenyl}cyclopropane-1,1-dicarboxylate, γmaxfilm 1740, 1720 cm-1, and dimethyl trans-3-methyl-2-(3-hydroxy-1,5-heptadienyl)cyclopropane-1,1-dicarboxylate (Example 58) gives dimethyl trans-2-{3-[(tetrahydropyran-2-yl)oxy]-1,5-heptadienyl}cyclopropane-1,1-dicarboxylate.
Sources & evidence
- ORD record
- ord-f06a5cf2e994428e96f492495e4a0a89
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04089898
Reaction notes
Loading…