Water → HCID 19886408, compound

HRID 2372746Notes

Reaction equation

HRID 2372746 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:15][C:16](O)=[O:17])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=1.O.[OH-].[Na+]>O1CCCC1>[C:7]1([CH2:15][CH2:16][OH:17])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21839742HCID 21839742, compound

Product 1

HCID 19886408HCID 19886408, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A three-necked flask is charged under a stream of nitrogen with 7.4 g of lithium aluminium hydride, and 70 ml of anhydrous tetrahydrofuran are then added. A solution of 2-benzocyclobuten-1-ylacetic acid (prepared according to the process described in J. Org. Chem., (1979), 44, p. 1036) in 120 ml of tetrahydrofuran is then introduced dropwise. The reaction solution is left stirring overnight. The flask is then cooled with an ice bath and the mixture is hydrolyzed by adding 6.6 ml of water, 6.6 ml of 4N sodium hydroxide and then 19.8 ml of water very gently. The complex is drained and washed with ethyl ether and the organic phase is dried over magnesium sulfate. After filtration, the filtrate is evaporated to dryness to obtain the expected compound.

Workup

  1. additionare then added
  2. waitThe reaction solution is left
  3. temperatureThe flask is then cooled with an ice bath
  4. washwashed with ethyl ether
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-25221dd2a74247a994aeb7724f4fcd7f
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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