Water → HCID 61088246, compound

HRID 1484531Notes

Reaction equation

HRID 1484531 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6]CCCCC.[CH:12]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[O:13].[OH2:19].C1[CH2:24][O:23][CH2:22][CH2:21]1>>[CH3:6][O:19][C:1]1[CH:21]=[C:22]([O:23][CH3:24])[CH:4]=[CH:3][C:2]=1[CH:12]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[OH:13]

Participants

6

Reactant 5

HCID 962WaterHCID 73642-ThiophenecarboxaldehydeHCID 8028TetrahydrofuranHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 61088246HCID 61088246, compound

Conditions

Temperature
-78 °C

Procedure

1.6 M solution of n-butyllithium in hexane (9.5 ml; 15.2 mmol; 1.1 eq) is added dropwise to a solution of compound (7) (3 g; 13.8 mmol; 1.0 eq) in 90 ml of anhydrous THF cooled to −78° C. The solution is stirred for 1 hour at −78° C. and then 2-formylthiophene (4.7 ml; 49.5 mmol; 3.6 eq) is added dropwise. The solution is stirred for 3 hours at 78° C., then for 15 hours at room temperature, and then 150 ml of water is added. After extraction with ethyl acetate (2×150 ml), the organic phases are combined, dried over MgSO4 and concentrated under reduced pressure. The oil obtained is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 10:0 to 8:2) to lead to a mixture of compound (8) and thiophene-2-methanol (3.3 g; 85% by mass of compound (8); 87%) obtained as a yellow oil.

Workup

  1. stirringThe solution is stirred for 3 hours at 78° C.
  2. waitfor 15 hours at room temperature
  3. extractionAfter extraction with ethyl acetate (2×150 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe oil obtained
  7. customis purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 10:0 to 8:2)
  8. additionto lead to a mixture of compound (8) and thiophene-2-methanol (3.3 g; 85% by mass of compound (8); 87%)
  9. customobtained as a yellow oil

Sources & evidence

ORD record
ord-11eaa85475b64d86b45e177f50a304ab
Source dataset
uspto-grants-2016_08
Patent number
US09422261B2

Reaction notes

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