Water → HCID 20636305, compound

HRID 49330Notes

Reaction equation

HRID 49330 reaction equation
[CH2:1]([C:3]1([C:8]2[S:12][C:11]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:25](OC)=[O:26])[C:18](=[CH:23][CH:24]=3)[C:19](OC)=[O:20])=[CH:10][CH:9]=2)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH2:1]([C:3]1([C:8]2[S:12][C:11]([CH2:13][O:14][C:15]3[CH:24]=[CH:23][C:18]([CH2:19][OH:20])=[C:17]([CH2:25][OH:26])[CH:16]=3)=[CH:10][CH:9]=2)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20636318Dimethyl 4-[5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienylmethoxy]phthalateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20636305HCID 20636305, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

12.7 g (31.5 mmol) of dimethyl 4-[5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienylmethoxy]phthalate are dissolved in 500 mL of anhydrous ethyl ether. 2.87 g (75.7 mmol) of lithium aluminium hydride are added and the reaction medium is stirred at 0° C. for 1 hour. 2.9 mL of water are then added slowly, followed by 2.9 mL of aqueous 15% sodium hydroxide, and then 8.7 mL of water are also added slowly. After stirring for 20 minutes, the medium is then filtered. The filtrate is concentrated under reduced pressure and the residue obtained is then purified by chromatography on a column of silica. A white solid (m.p.: 78-80° C.) is obtained (m=8 g; Y=72%).

Workup

  1. stirringAfter stirring for 20 minutes
  2. filtrationthe medium is then filtered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue obtained
  5. customis then purified by chromatography on a column of silica

Sources & evidence

ORD record
ord-156cf9c097f2409eb13efe01dc7132cb
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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