Diethyl Ether → (1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl)methanol

HRID 2167368Notes

Reaction equation

HRID 2167368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[C:9]2[C:17](OC)=[O:18])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(OCC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[C:9]2[CH2:17][OH:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 90406393methyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 90404801(1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product prepared in Step C (500 mg, 1.48 mmol, 1 eq) in THF (10 mL) at 0° C. under N2 was added LAH (1.48 mL of a 2 M solution in THF, 2.96 mmol, 2 eq). After 1 hr, saturated sodium potassium tartrate (5 mL) was added dropwise at first, the solution was warmed to room temperature, diethyl ether was added, the solution decanted from the solid, washed with brine, dried over MgSO4 and concentrated to yield (1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl)methanol.

Workup

  1. customthe solution decanted from the solid
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-626809ffe34c48ca981ed314b8e6c03e
Source dataset
uspto-grants-2015_06
Patent number
US09045454B2

Reaction notes

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