1,2-Dimethoxyethane → HCID 86740522, compound

HRID 65541Notes

Reaction equation

HRID 65541 reaction equation
[H-].[Na+].COP(=O)[O:6][CH3:7].[O:9]=[C:10]([CH:12]([CH3:17])[CH2:13][C:14]#[C:15][CH3:16])[CH3:11].[CH2:18]([CH2:21]OC)[O:19]C>>[O:9]=[C:10]([CH:12]([CH3:17])[CH2:13][C:14]#[C:15][CH3:16])[CH:11]=[CH:15][CH:14]([CH2:13][CH:12]=[CH:10][CH3:11])[CH2:21][C:18]([O:6][CH3:7])=[O:19]

Participants

4

Reactant 3

HCID 80711,2-Dimethoxyethane3×HCID 24758Sodium hydrideHCID 178443813HCID 178443813, compound

Product 1

HCID 86740522HCID 86740522, compound

Procedure

To a slurry of 301.6 mg of 50% sodium hydride in mineral oil and 150 ml of anhydrous dimethoxyethane (DME) is added 1.32 g (5.7 mmole) of 2-oxo-3-methylhept-5-yne dimethylphosphonate (prepared as described in U.S. Pat. No. 4,235,930) in 15 ml of DME at 0° C. under an argon atmosphere. The mixture is stirred at 25° for 1.5 hours. To the solution at 25° is added 1.05 g (3.9 mmole) of [1β,2β(5Z),3α,4β]-7-[3-formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester (prepared as described in Example 1), in 15 ml of DME. After 1 hour the reaction is quenched with 0.7 ml of glacial acetic acid, concentrated, dissolved in 500 ml of ether, washed with three 100 ml portions of 5% NaHCO3 and 100 ml of brine. The organic layer is dried over MgSO4 and concentrated to give 1.66 g of crude title A compound.

Workup

  1. customprepared
  2. customat 0° C.
  3. customAfter 1 hour the reaction is quenched with 0.7 ml of glacial acetic acid
  4. concentrationconcentrated
  5. dissolutiondissolved in 500 ml of ether
  6. washwashed with three 100 ml portions of 5% NaHCO3 and 100 ml of brine
  7. dry with materialThe organic layer is dried over MgSO4
  8. concentrationconcentrated
  9. customto give 1.66 g of crude title A compound

Sources & evidence

ORD record
ord-e780afb5a49d49458d025524497a6d63
Source dataset
uspto-grants-1986_09
Patent number
US04614825

Reaction notes

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