Water → (E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethyloct-6-en-3-ol

HRID 49323Notes

Reaction equation

HRID 49323 reaction equation
[CH2:1]([C:3]([OH:32])([CH2:30][CH3:31])[CH2:4][CH2:5]/[CH:6]=[C:7](/[C:9]1[S:13][C:12]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([C:26](OC)=[O:27])[C:19](=[CH:24][CH:25]=2)[C:20](OC)=[O:21])=[CH:11][CH:10]=1)\[CH3:8])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[OH:27][CH2:26][C:18]1[CH:17]=[C:16]([CH:25]=[CH:24][C:19]=1[CH2:20][OH:21])[O:15][CH2:14][C:12]1[S:13][C:9](/[C:7](/[CH3:8])=[CH:6]/[CH2:5][CH2:4][C:3]([CH2:30][CH3:31])([OH:32])[CH2:1][CH3:2])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15516125dimethyl 4-[5-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)-2-thienylmethoxy]phthalateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10111871(E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethyloct-6-en-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

350 mg (0.76 mmol) of dimethyl 4-[5-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)-2-thienylmethoxy]phthalate are dissolved in 20 mL of anhydrous ethyl ether. 70 mg (1.8 mmol) of lithium aluminium hydride are added and the reaction medium is stirred at room temperature for 30 minutes. 400 mL of water are then added slowly and the medium is filtered. The filtrate is concentrated under reduced pressure and the residue obtained is then purified by chromatography on a column of silica (eluent: 70 ethyl acetate/30 heptane). A white solid (m.p.: 100-102° C.) is obtained (m=175 mg; Y=58%).

Workup

  1. filtrationthe medium is filtered
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue obtained
  4. customis then purified by chromatography on a column of silica (eluent: 70 ethyl acetate/30 heptane)

Sources & evidence

ORD record
ord-ff66c071e48c4708934910615263cea6
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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