Diethyl Ether → HCID 54120801, compound

HRID 846619Notes

Reaction equation

CCOCC.[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 ether solution containing 6.8 g of ethyl 4-(2-tetrahydropyranyloxy)cinnamate was added dropwise to an anhydrous ether solution containing 0.47 g of lithium aluminium hydride being cooled at -30° C. After the 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 a saturated aqueous solution of sodium sulfate was gradually added to the reaction mixture, and the precipitates formed 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 addition
customwas gradually elevated up to -10° C.
customthe precipitates formed
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-0eed660676c8472fbe4556717eb9e73f
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05137889

Reaction notes

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