Sodium sulfate decahydrate → 3-Methylbenzo(b)thiophene-2-methanol

HRID 1173820Notes

Reaction equation

HRID 1173820 reaction equation
[CH3:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 268658Methyl 3-methylbenzo[b]thiophene-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 6012933-Methylbenzo(b)thiophene-2-methanolYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of methyl 3-methylbenzo[b]thiophen-2-carboxylate (5.00 g, 24.2 mmol) in THF (25 mL) dropwise to a 1M solution of lithium aluminum hydride in THF (121 mL, 121 mmol) at 0° C. Stir 1 hour. Add an excess of sodium sulfate decahydrate portionwise (slowly at first), stir for 30 minutes at 0° C., then 2 hours at room temperature. Filter, and wash the cake with THF. Concentrate the combined filtrates to afford the drawn product as a white solid (3.60 g, 83%): 1H NMR (CDCl3) δ 7.81 (m, 1H), 7.68 (m, 1H), 7.35 (m, 2H), 4.92 (d, 2H), 2.40 (s, 3H), 1.77 (t, 1H).

Workup

  1. stirringstir for 30 minutes at 0° C.
  2. custom2 hours
  3. customat room temperature
  4. filtrationFilter
  5. washwash the cake with THF
  6. concentrationConcentrate the combined filtrates

Sources & evidence

ORD record
ord-b57bb2b6f4474dd8ac517aedd1a8a867
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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