Diethyl Ether → HCID 54120801, compound

HRID 2291350Notes

Reaction equation

C(OCC)C.[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][C:13]1[CH:25]=[CH:24][C:16]([CH:17]=[CH:18][C:19](OCC)=[O:20])=[CH:15][CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][C:13]1[CH:14]=[CH:15][C:16]([CH:17]=[CH:18][CH2:19][OH:20])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: -30 °C

Procedure

50 Milliliters of anhydrous diethyl ether solution containing 6.8 g of ethyl 4-(2-tetrahydropyranyloxy)cinnamate was added dropwise to an anhydrous diethyl ether solution being cooled at -30° C. containing 0.47 g of lithium aluminium hydride. After the dropwise addition was finished, the reaction mixture was stirred for 1 hour at the same temperature, then the temperature of the reaction mixture was gradually elevated up to -10° C., then an aqueous solution saturated with sodium sulfate was gradually added to the reaction mixture, and the precipitates formed in the reaction mixture were removed by filtration. The filtrate was dried with anhydrous sodium sulfate, then concentrated to dryness, the residue thus obtained was treated by means of silica gel column chromatography (eluent: chloroform) to yield 3.2 g of 4-(2-tetrahydropyranyloxy)cinnamyl alcohol in the form of colorless oily substance. Refractive index: nD22 1.5520.

Workup

additionAfter the dropwise addition
customwas gradually elevated up to -10° C.
customthe precipitates formed in the reaction mixture
customwere removed by filtration
dry with materialThe filtrate was dried with anhydrous sodium sulfate
concentrationconcentrated to dryness
customthe residue thus obtained

Sources & evidence

ORD record: ord-278aa5aecc5f45e483c34767f23d27e2
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04795814

Reaction notes

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