Hydrochloric Acid → HCID 20060158, compound

HRID 1085488Notes

Reaction equation

HRID 1085488 reaction equation
[CH2:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH2:19][CH3:20])(O)[CH2:9][CH2:10][CH2:11][OH:12])[CH3:2].Cl.O1CCCC1>C(O)C>[CH2:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH2:19][CH3:20])=[CH:9][CH2:10][CH2:11][OH:12])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 20060177HCID 20060177, compound

Product 1

HCID 20060158HCID 20060158, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

This oil consisting of 1,1-bis(3-ethyl-2-thienyl)-1,4-dihydroxylbutan was mixed with 75 ml 2N hydrochloric acid solution, 75 ml tetrahydrofuran and 75 ml ethanol and heated at 50° C. for 18 h. The solution was evaporated and the resultant oil was purified by "flash" chromatography on silica gel (Art 9385) eluting with heptane/ethylacetate (5:1) to give 4,4-bis(3-ethylthien-2-yl)but-3-en-1-ol (5.4 g, 69%) as an oil.

Workup

  1. customThe solution was evaporated
  2. customthe resultant oil was purified by "flash" chromatography on silica gel (Art 9385)
  3. washeluting with heptane/ethylacetate (5:1)

Sources & evidence

ORD record
ord-df4fb941a3694ca497a5c3a056b62224
Source dataset
uspto-grants-1991_04
Patent number
US05010090

Reaction notes

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