Ethanol → (E)-3-(4-Benzyloxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-acrylic Acid Ethyl Ester

HRID 1726987Notes

Reaction equation

HRID 1726987 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12]([CH:19]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][CH2:22][O-:23].[Na+].[CH2:25]([OH:27])[CH3:26]>>[CH2:22]([O:23][C:25](=[O:27])/[CH:26]=[CH:19]/[C:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 226476154-Benzyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxaldehyde

Product 1

HCID 69035743(E)-3-(4-Benzyloxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-acrylic Acid Ethyl Ester

Procedure

To a cooled suspension (−10° C.) of 0.9 g (3.38 mmol) of 4-benzyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxaldehyde [PCT Int. Appl. (2002), WO2002/092084A1] in 10 ml of absolute ethanol were added successively 0.75 ml (3.7 mmol) of triethyl phosphonoacetate and 0.255 g (3.7 mmol) of powdered sodium ethylate. Then, the mixture was stirred at ambient temperature for 1 hour. Subsequently, the reaction mixture was poured onto crushed ice/diluted hydrochloric acid and the product was extracted twice with tert.-butyl methyl ether; the organic phase was washed with brine and dried over anhydrous sodium sulfate, and finally evaporated leaving 1.15 g of the title compound as light brown solid.

Workup

  1. additionSubsequently, the reaction mixture was poured
  2. customonto crushed ice/diluted hydrochloric acid
  3. extractionthe product was extracted twice with tert.-butyl methyl ether
  4. washthe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfinally evaporated

Sources & evidence

ORD record
ord-c5bc37097fcb4d1c9c4afbaa931dc9ab
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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