Tetrahydropyranyl ether → HCID 20326977, compound

HRID 614303Notes

Reaction equation

HRID 614303 reaction equation
[OH:1][C:2](C)([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])/[CH:3]=[CH:4]/[CH:5]1[CH2:7][C:6]1([C:13]([O:15][CH2:16]C)=[O:14])[C:8]([O:10][CH2:11]C)=[O:9].O1CCC[CH2:26][CH:25]1OC1CCCCO1.[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.[CH3:43][CH2:44]OCC.[OH:48][CH:49]([CH:65]([CH3:70])[CH2:66][CH2:67][CH2:68][CH3:69])/[CH:50]=[CH:51]/[CH:52]1[CH2:54][C:53]1([C:60]([O:62][CH2:63][CH3:64])=[O:61])[C:55]([O:57][CH2:58][CH3:59])=[O:56]>>[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[O:48][CH:49]([CH:65]([CH3:70])[CH2:66][CH2:67][CH2:68][CH3:69])/[CH:50]=[CH:51]/[CH:52]1[CH2:54][C:53]1([C:55]([O:57][CH2:58][CH3:59])=[O:56])[C:60]([O:62][CH2:63][CH3:64])=[O:61].[CH2:25]([CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:43][CH3:44])[CH:2]([OH:1])/[CH:3]=[CH:4]/[CH:5]1[CH2:7][C:6]1([C:8]([O:10][CH3:11])=[O:9])[C:13]([O:15][CH3:16])=[O:14])[CH3:26]

Participants

6

Reactant 4

HCID 263182Tetrahydropyranyl etherHCID 21328844HCID 21328844, compoundHCID 21328846HCID 21328846, compoundHCID 66693921HCID 66693921, compound

Product 2

HCID 20326977HCID 20326977, compoundHCID 21328847HCID 21328847, compound

Procedure

In the same manner but using an equivalent amount of one of the compounds of formula 1 (R2 = H), for example, the compounds listed in Examples 17 to 40, instead of diethyl trans-2-(3-hydroxy-3-methyl-1-octenyl)cyclopropane-1,1-dicarboxylate, then the corresponding tetrahydropyranyl ether compound of formula 1 (R2 = tetrahydropyranyl) is obtained, for example, the corresponding tetrahydropyran ether compounds of Examples 17 to 40, respectively. More specifically exemplified, in the same manner diethyl trans-2-(3-hydroxy-4-methyl-1-octenyl)cyclopropane-1,1-dicarboxylate, described in Example 17 gives diethyl trans-2-{3-[(tetrahydropyran-2-yl)oxy]-4-mehyl-1-octenyl}cyclopropane-1,1-dicarboxylate, νmaxfilm 1035, 1140, 1220 cm-1, and dimethyl trans-2-(4-ethyl-3-hydroxy-1-decenyl)cyclopropane-1,1-dicarboxylate, described in Example 24, gives dimethyl trans-2-{4-ethyl-3-[(tetrahydropyran-2-yl)oxy]-1-decenyl}cyclopropane-1,1-dicarboxylate.

Sources & evidence

ORD record
ord-9e80c1cb74e74782b576b3f3f652ed40
Source dataset
uspto-grants-1979_03
Patent number
US04144251

Reaction notes

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