Hydrochloric Acid → 4-(Thiophen-2-yl)butan-1-ol

HRID 2417286Notes

Reaction equation

HRID 2417286 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.Cl.C(OCC)C>C1COCC1>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 1407664-(2-Thienyl)butanoic acid methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 126238624-(Thiophen-2-yl)butan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2.5 M solution of lithium aluminum hydride in THF (10 mL) was slowly added to a solution of methyl ester 1b (7.30 g, 0.04 mol,) in 100 mL of anhydrous THF. After completion of the addition, the solution was refluxed for four hours, then cooled to room temperature. Hydrochloric acid (10%, 25 mL) was then slowly added, and the resulting mixture was heated for another 30 minutes. After cooling to room temperature, diethyl ether (100 mL) was added, the organic layer was separated and washed with brine, dried with anhydrous magnesium sulfate. Evaporation of the solvent gave the alcohol 1c (5.4 g, 90%) as a colorless oil. 1H NMR (250 MHz, 25° C., CDCl3): δ 7.12 (m, 1H, Ar—H), 6.92 (m, 1H, Ar—H), 6.79 (m, 1H, Ar—H), 3.62 (t, 2H, CH2OH), 2.86 (t, 2H, Ar—CH2), 2.30 (s, 1H, OH), 2.00 (m, 4H, CH2CH2CH2CH2).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe solution was refluxed for four hours
  3. temperaturethe resulting mixture was heated for another 30 minutes
  4. temperatureAfter cooling to room temperature
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-64fa10f8b8464826bcf409e22293a509
Source dataset
uspto-grants-2004_11
Patent number
US06825358B2

Reaction notes

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