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

HRID 978673Notes

Reaction equation

HRID 978673 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

5

Reactant 3

HCID 7707BenzenepropanalHCID 18997637(8-Tetrahydropyranyloxyoctyl)triphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 536773642-(11-Phenyl-8-undecenyloxy)-tetrahydropyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. temperatureto warm to room temperature
  2. customevaporated
  3. extractionThe residue was extracted with ether
  4. extractionthe extract again
  5. customevaporated
  6. customthe residue was chromatographed on silica-gel
  7. washeluting with 1:1 ether

Sources & evidence

ORD record
ord-4e838d82dfed4afb8d7d65b3694ea148
Source dataset
uspto-grants-1987_05
Patent number
US04665189

Reaction notes

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