Citric Acid → 8-Cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

HRID 1948146Notes

Reaction equation

[CH:1]1([CH2:4][C:5]2([C:15]#N)[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[O:17]1C2(CCC(C#N)CC2)OCC1.C1(CBr)CC1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH:1]1([CH2:4][C:5]2([CH:15]=[O:17])[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile, prepared from 1,4-dioxa-spiro[4.5]decane-8-carbonitrile and cyclopropylmethyl bromide in a similar fashion as described for 5, (3.00 g, 13.6 mmol) in tetrahydrofuran (40 mL) at −78° C. was added a 1M solution of diisobutylaluminium hydride in toluene (20.3 mL, 20.3 mmol, 1.5 eq.) and the reaction was allowed to warmed to 0° C. over a period of 3 h. The mixture was recooled to −78° C., neutralized by dropwise addition of a 10% aqueous citric acid solution and warmed to room temperature. The mixture was partitioned between methyl-tert.butyl ether and water, the aqueous phase extracted twice with methyl-tert.butyl ether and the combined organics were dried over magnesium sulphate, filtered and evaporated to give 8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde.

Workup

customwas recooled to −78° C.
temperaturewarmed to room temperature
customThe mixture was partitioned between methyl-tert.butyl ether and water
extractionthe aqueous phase extracted twice with methyl-tert.butyl ether
dry with materialthe combined organics were dried over magnesium sulphate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-11b3c49a34aa44c298b233bf87529397
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399482B2

Reaction notes

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