Water → 8-(2-Cyclopentyl-ethylidene)-1,4-dioxa-spiro[4.5]decane

HRID 2392763Notes

Reaction equation

Cl.[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12](C3C=CC=C(OC)C=3)([OH:15])[CH:11](CN(C)C)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:28][C:29]([O-:32])(C)C.[K+].O1C2(CCC(=O)CC2)OCC1.O>C1(C)C=CC=CC=1>[CH:2]1([CH2:7][CH:8]=[C:9]2[CH2:10][CH2:11][C:12]3([O:15][CH2:28][CH2:29][O:32]3)[CH2:13][CH2:14]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

The reaction was conducted in a nitrogen atmosphere with the exclusion of moisture. 21.9 g (50 mmole) of compound (52) were added to 5.6 g (50 mmole) potassium tert-butylate in 400 ml toluene. The mixture was stirred for 30 minutes at room temperature and for 1 hour at 80° C., and was subsequently cooled to 60° C. 7.8 g (50 mmole) 1.4-dioxa-spiro[4.5]decan-8-one were added. The mixture was then stirred for 18 hours at 60° C. and cooled. 100 ml water were added drop-wise. The organic phase was separated off, the aqueous phase was extracted twice with toluene and dried over sodium sulphate, and the solvent was removed by distillation. 29 g oil were obtained, which was purified with 1:4 diisopropyl ether/n-hexane on a silica gel column.

Workup

temperaturewas subsequently cooled to 60° C
stirringThe mixture was then stirred for 18 hours at 60° C.
temperaturecooled
customThe organic phase was separated off
extractionthe aqueous phase was extracted twice with toluene
dry with materialdried over sodium sulphate
customthe solvent was removed by distillation

Sources & evidence

ORD record: ord-e35f16f36b5f4b249f7472c7f067843d
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05801201

Reaction notes

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