Acetic Acid → HCID 68119904, compound

HRID 1415320Notes

Reaction equation

HRID 1415320 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C[C:7]([CH3:23])(P(=O)([O-])[O-])[C:8](=[O:18])[CH:9]1[O:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10]1.[CH2:24]([CH2:27][O:28][CH3:29])OC.[C:30]([OH:33])(=[O:32])[CH3:31].[OH2:34]>CCCCCC>[O:18]=[C:8]([CH:9]1[O:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:17]1)/[CH:7]=[CH:23]/[C@H:1]1[C@H:29]([O:28][C:27](=[O:34])[C:24]2[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=2)[CH2:4][C@H:3]2[C@@H:2]1[CH2:31][C:30](=[O:33])[O:32]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 80711,2-Dimethoxyethane2×HCID 86734435HCID 86734435, compoundHCID 178418339Butyllithium

Product 1

HCID 68119904HCID 68119904, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

At -70° C., 0.6 ml. of a 2-molar butyllithium solution in hexane was added dropwise to a solution of 299 mg. of dimethyl-2-oxo-2-(1,3-dioxa-2-indanyl)-ethylphosphonate in 6 ml. of absolute dimethoxyethane; the mixture was warmed to room temperature, and 274 mg. of the above-mentioned 6-formyl compound, dissolved in 5 ml. of absolute dimethoxyethane, was added thereto. The reaction mixture was agitated for 1 hour at room temperture. After neutralization with glacial acetic acid, the mixture was combined with water, extracted with ether, shaken with sodium bicarbonate solution and water, dried over magnesium sulfate, and evaporated under vacuum. The residue was recrystallized from isopropyl ether/methylene chloride, thus obtaining 220 mg. of crystals, m.p. 119°-120° C.

Workup

  1. customAt -70° C.
  2. extractionextracted with ether
  3. stirringshaken with sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe residue was recrystallized from isopropyl ether/methylene chloride
  7. customthus obtaining 220 mg

Sources & evidence

ORD record
ord-8d38dd070f6e49169c16bf381da7146b
Source dataset
uspto-grants-1977_01
Patent number
US04004020

Reaction notes

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