Hydrochloric Acid → 2-Hydoxymethyl-5-thiophen-3-yl-benzofuran

HRID 970795Notes

Reaction equation

HRID 970795 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([C:14](O)=[O:15])=[CH:11][C:10]=3[CH:17]=2)=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[OH:15][CH2:14][C:12]1[O:13][C:9]2[CH:8]=[CH:7][C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[CH:17][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12990911HCID 12990911, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 129909122-Hydoxymethyl-5-thiophen-3-yl-benzofuranYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 5-thiophen-3-yl-benzofuran-2-carboxylic acid 21 (0.84 g, 3.4 mmole) dissolved in THF (30 ml) was cooled to 5° C., LiAlH4 (0.26 g, 6.9 mmole) was added portionwise. The solution was then stirred at ambient temperature for 2 hrs. After addition of 1 M HCl, the mixture was extracted , washed, dried, evaporated, and the residue was purified by chromatography to give about 0.368 g of 2-hydroxymethyl-5-thiophen-3-yl-benzofuran 22, mp. 122-124° C.

Workup

  1. extractionthe mixture was extracted
  2. washwashed
  3. customdried
  4. customevaporated
  5. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-081e8de0983645d0b5feb2c5e6c26fc1
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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