2-Bromo-3-methylthiophene → HCID 68842710, compound

HRID 1432600Notes

Reaction equation

HRID 1432600 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[Li+].CC([N-]C(C)C)C.[O:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1>C1COCC1>[Br:1][C:2]1[S:3][C:4]([C:19]2([OH:22])[CH2:20][CH2:21][O:16][CH2:17][CH2:18]2)=[CH:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 843142-Bromo-3-methylthiopheneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 68842710HCID 68842710, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of 2-bromo-3-methyl-thiophene (2.0 g, 17.75 mmol) and THF (30 mL) is added 2.0 M LDA (9.32 mL, 18.63 mmol). After 30 minutes at −78° C. tetrahydro-pyran-4-one (2.3 mL, 23.07 mmol) is added and the solution is warmed to ambient temperature. The solution is washed with sat. NH4Cl (30 mL). The aqueous phases is extracted with EtOAc. The combined organic layers are dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (30%-100% EtOAc/hexane gradient) furnish the title compound (2.3 g, 8.30 mmol, 47%). 1H NMR (CDCl3), δ 1.82 (m, 2H), 2.00 (s, 3H), 2.06-2.15 (m, 3H), 2.16 (s, 3H), 3.77-3.84 (m, 2H), 3.87 dt, J=11.3, 2.2 Hz, 2H), 6.67 (s, 1H). LC/MS (m/z): calcd. for C10H13BrO2S (M+H)+: 277.0; found: 260.9.

Workup

  1. washThe solution is washed with sat. NH4Cl (30 mL)
  2. extractionThe aqueous phases is extracted with EtOAc
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by ISCO column chromatography (30%-100% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-a67dbcf1b7954558b27beded355d345d
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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