Acetic Acid → 3,4-Di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde

HRID 442436Notes

Reaction equation

HRID 442436 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:11][CH:10]([C:20]#N)[CH:9]1[CH2:22][CH2:23][CH:24]([O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[H-].C([Al+]CC(C)C)C(C)C.C(O)(=[O:49])C>C(OCC)C.C1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:11][CH:10]([CH:20]=[O:49])[CH:9]1[CH2:22][CH2:23][CH:24]([O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 21225700DiisobutylaluminumhydrideHCID 86732993HCID 86732993, compound

Product 1

HCID 544198253,4-Di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a vigorously stirred solution of crude 3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbonitrile (7.9 g.) [prepared as described in (l) above] in dry diethyl ether (50 ml.) was added a solution of di-isobutylaluminium hydride (4.6 g.) in dry benzene (20 ml.) at 3°-7° C. The mixture was stirred at room temperature for 15 minutes and then added with stirring to aqueous 2N acetic acid solution (75 ml.) at below 15° C. The organic phase was separated, and the aqueous layer extracted with diethyl ether. The combined organic phases were washed with aqueous sodium bicarbonate and with water, dried over magnesium sulphate, and the solvents removed in vacuo to give crude 3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde (7.7 g.), which was used as starting material in the following preparation (n) of ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}hepta-2,4,6-trienoate without further purification.

Workup

  1. additionadded
  2. customThe organic phase was separated
  3. extractionthe aqueous layer extracted with diethyl ether
  4. washThe combined organic phases were washed with aqueous sodium bicarbonate and with water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-29cbcc16b7b047329e8b12638221172c
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Reaction notes

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