Water → (E)-7-[4-(3,4-bis-Hydroxymethyl-phenoxymethyl)2-thienyl]-3-ethylnon-6-en-3-ol

HRID 49349Notes

Reaction equation

HRID 49349 reaction equation
[CH2:1](/[C:3](/[C:13]1[S:17][CH:16]=[C:15]([CH2:18][O:19][C:20]2[CH:21]=[C:22]([C:30](OC)=[O:31])[C:23](=[CH:28][CH:29]=2)[C:24](OC)=[O:25])[CH:14]=1)=[CH:4]\[CH2:5][CH2:6][C:7]([CH2:11][CH3:12])([OH:10])[CH2:8][CH3:9])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[OH:31][CH2:30][C:22]1[CH:21]=[C:20]([CH:29]=[CH:28][C:23]=1[CH2:24][OH:25])[O:19][CH2:18][C:15]1[CH:14]=[C:13](/[C:3](/[CH2:1][CH3:2])=[CH:4]/[CH2:5][CH2:6][C:7]([CH2:11][CH3:12])([OH:10])[CH2:8][CH3:9])[S:17][CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69928788dimethyl 4-[5-((E)-1,5-diethyl-5-hydroxyhept-1-enyl)-3-thienylmethoxy]phthalate

Product 1

HCID 69825683(E)-7-[4-(3,4-bis-Hydroxymethyl-phenoxymethyl)2-thienyl]-3-ethylnon-6-en-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

480 mg (1.1 mmol) of dimethyl 4-[5-((E)-1,5-diethyl-5-hydroxyhept-1-enyl)-3-thienylmethoxy]phthalate are dissolved in 10 mL of ethyl ether. This solution is added to a suspension of 130 mg (3.4 mmol) of lithium aluminium hydride and the reaction medium is stirred for 15 minutes. The reaction medium is then treated by successive addition of 130 μL of water, 130 μL of 15% sodium hydroxide and 400 μL of water. After filtration and chromatography on silica gel (eluent: 2 heptane/8 ethyl acetate), the desired product is obtained in the form of white crystals (m.p.=63-64° C.; m=380 mg; Y=90%).

Workup

  1. filtrationAfter filtration and chromatography on silica gel (eluent: 2 heptane/8 ethyl acetate)

Sources & evidence

ORD record
ord-2a1116e8340448ef9a453a4fdc4dcd4c
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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