Triethylamine → HCID 57989255, compound

HRID 1689552Notes

Reaction equation

HRID 1689552 reaction equation
[Cl-].[Li+].C(N([CH2:8][CH3:9])CC)C.[CH3:10][C:11]([CH3:26])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[CH:12]=O.[Cl-].[NH4+]>C(#N)C.O.CCOCC>[CH3:10][C:11]([CH3:26])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)/[CH:12]=[CH:25]/[C:20]([O:21][CH2:8][CH3:9])=[O:19]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 86636759HCID 86636759, compound

Product 1

HCID 57989255HCID 57989255, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of triethyl phosphonoacetate (1.62 mL) in acetonitrile (8 mL) was treated with lithium chloride (0.43 g) and then cooled to 0° C. and triethylamine (1.23 mL) added dropwise as a solution in acetonitrile (2.5 mL). The reaction mixture was stirred at 0° C. for 15 minutes then a solution of 2,2-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptanal (1.65 g) in acetonitrile (6 mL) was added. The resultant mixture was allowed to warm to room temperature and was stirred for 3 hours before treating with saturated aqueous ammonium chloride solution, ether and water. The layers were separated and the aqueous phase was extracted with ether (×2) and the combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated to afford the crude product. Purification was by silica gel chromatography eluting with 0 to 40% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless oil. Yield 0.89 g.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 3 hours
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ether (×2)
  5. washthe combined organics were washed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto afford the crude product
  10. customPurification
  11. washeluting with 0 to 40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-a81fc50f7bcc4ef49c9687ac78977779
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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