Sodium hydride → HCID 86751756, compound

HRID 398314Notes

Reaction equation

HRID 398314 reaction equation
[H-].[Na+].[C:3]([C:8]1[CH:22]=[CH:21][C:11]([CH2:12]P(=O)(OCC)OCC)=[CH:10][CH:9]=1)([O:5][CH2:6][CH3:7])=[O:4].[CH:23]([C:25]1[C:34]([O:35][CH2:36][C:37]#[C:38][CH2:39][CH3:40])=[CH:33][C:32]2[C:31]([CH3:42])([CH3:41])[CH2:30][CH2:29][C:28]([CH3:44])([CH3:43])[C:27]=2[CH:26]=1)=O>CN(C=O)C>[CH2:36]([O:35][C:34]1[C:25](/[CH:23]=[CH:12]/[C:11]2[CH:10]=[CH:9][C:8]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:22][CH:21]=2)=[CH:26][C:27]2[C:28]([CH3:44])([CH3:43])[CH2:29][CH2:30][C:31]([CH3:42])([CH3:41])[C:32]=2[CH:33]=1)[C:37]#[C:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10979490Ethyl 4-((diethoxyphosphoryl)methyl)benzoateHCID 23002494HCID 23002494, compound

Product 1

HCID 86751756HCID 86751756, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

193 mg of NaH (55% in mineral oil) were placed in 10 ml of abs. DMF under argon and 1.66 g of diethyl (4-carbethoxybenzyl)-phosphonate were added thereto at 0° and the mixture was subsequently stirred at room temperature until the H2 evolution had finished. Then, 1.08 g of 2-formyl-3-pent-2-ynyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene without addition solvent were added at 0°. After 30 min. at room temperature the mixture was extracted with hexane and washed twice with ethanol/H2O=8/2. Drying, evaporation and direct crystallization from hexane yielded 1.45 g of ethyl (E)-4-[2-(3-pent-2-ynyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoate as yellowish crystals of m.p. 80-82°.

Workup

  1. additionwere added at 0°
  2. extractionAfter 30 min. at room temperature the mixture was extracted with hexane
  3. washwashed twice with ethanol/H2O=8/2
  4. customDrying
  5. customevaporation and direct crystallization from hexane

Sources & evidence

ORD record
ord-eefa2d4bb40a44f4890c65f97f8a9bbc
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

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