Benzenepropanal → 2-(11-Phenyl-8-undecenyloxy)-tetrahydropyran

HRID 1709075Notes

Reaction equation

C([Li])CCC.[Br-].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:41]1([CH2:47][CH2:48][CH:49]=O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1>[C:41]1([CH2:47][CH2:48][CH:49]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:13][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:7]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

Conditions

Temperature: -70 °C

Procedure

n-Butyl lithium (1.6M solution in hexane, 20 ml) was added to a stirred solution of the product of step (a) (11.0 g) in dry tetrahydrofuran at -70° C. under nitrogen. The orange solution was stirred for 30 minutes at -70° C. then a solution of 3-phenyl-propionaldehyde (2.75 g) in tetrahydrofuran (7 ml) was added. The pale solution was allowed to warm to room temperature and then evaporated. The residue was extracted with ether and the extract again evaporated and the residue was chromatographed on silica-gel eluting with 1:1 ether:hexane to give the title compound as a pale oil.

Workup

temperatureto warm to room temperature
customevaporated
extractionThe residue was extracted with ether
extractionthe extract again
customevaporated
customthe residue was chromatographed on silica-gel
washeluting with 1:1 ether

Sources & evidence

ORD record: ord-c524e8885b2944eb8261a0a3c2214a1d
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE033300

Reaction notes

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