Water → HCID 22345598, compound

HRID 584318Notes

Reaction equation

HRID 584318 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]([CH2:27][CH2:28][C:29]4[CH:30]=[C:31]([C:39](OC)=[O:40])[C:32](=[CH:37][CH:38]=4)[C:33](OC)=[O:34])[CH:21]=3)=[C:16]([CH2:43][CH2:44][CH3:45])[CH:15]=2)[O:13][CH2:12][CH2:11][O:10]1)[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH2:7]([C:9]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]([CH2:27][CH2:28][C:29]4[CH:38]=[CH:37][C:32]([CH2:33][OH:34])=[C:31]([CH2:39][OH:40])[CH:30]=4)[CH:21]=3)=[C:16]([CH2:43][CH2:44][CH3:45])[CH:15]=2)[O:10][CH2:11][CH2:12][O:13]1)[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22345596HCID 22345596, compound

Product 1

HCID 22345598HCID 22345598, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

182 mg (4.8 mmol) of lithium aluminum hydride are placed in 20 ml of dry THF in a round-bottomed flask and under nitrogen. At 0° C., a solution of 640 mg (1.2 mmol) of dimethyl 4-{2-[4′-(2-ethyl[1,3]dioxolan-2-yl)-6-methyl-2′-propylbiphenyl-3-yl]ethyl}phthalate in 5 ml of THF is added dropwise. The reaction medium is stirred for 1 hour at room temperature. 200 μl of water are then added very slowly, followed by addition of 200 μl of 15% sodium hydroxide solution and then 600 μl of water. The medium is filtered and the filtrate is evaporated to dryness. 640 mg (100%) of the expected product are obtained in the form of a colorless oil.

Workup

  1. filtrationThe medium is filtered
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-d2ee9dc199e64033b5fe297dbb5586c2
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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