Water → HCID 86749779, compound

HRID 1871250Notes

Reaction equation

HRID 1871250 reaction equation
[H-].[Na+].[CH3:3][C:4](P(OC)(O)=O)([C:6]([O-])=O)[CH3:5].[C:14]1(=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1.[OH2:24].[O:25]1[CH2:29][CH2:28]C[CH2:26]1>>[C:4]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)/[C:14](=[CH:28]/[C:29]([O:25][CH3:26])=[O:24])/[CH2:15][CH2:16]2)([CH3:6])([CH3:5])[CH3:3]

Participants

6

Reactant 5

HCID 962WaterHCID 67351-IndanoneHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 86749779HCID 86749779, compound

Procedure

To a suspension of sodium hydride (3.6 g of a 50% dispersion in oil, 75 mmole) previously washed with petroleum ether 30-50, in 100 ml of tetrahydrofuran (THF), there were added dropwise at 10-20° 13.8 g (75 mmole) of trimethylphosphonoacetate in 100 ml of THF. 15 min after the end of the addition, there was added to the reaction mixture, at 11-15°, a solution of the above-cited indanone (10.2 g, 55 mmole) in THF (150 ml). The mixture was kept under stirring for 16 h at 25°, then it was poured on 500 ml of water and extracted with ether. The combined organic extracts were washed with brine (2 times), dried (Na2SO4) and concentrated until forming an oil which became solid (12.6 g; isomer mixture). This product was crystallized in ether at -30°, to provide 5.56 g of methyl (E)-(5-tert-butyl-1-indanylidene)acetate.

Workup

  1. washpreviously washed with petroleum ether 30-50, in 100 ml of tetrahydrofuran (THF)
  2. addition15 min after the end of the addition, there
  3. additionwas added to the reaction mixture, at 11-15°
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with brine (2 times)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customuntil forming an oil which
  9. customThis product was crystallized in ether at -30°

Sources & evidence

ORD record
ord-c5818d5c5d844d7ca6d47028fe22d105
Source dataset
uspto-grants-2000_08
Patent number
US06103688

Reaction notes

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