Boron Trichloride → 2,2,2-trifluoro-N-(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide

HRID 1168881Notes

Reaction equation

HRID 1168881 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]([CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19]C)=[CH:14][CH:15]=2)[CH2:10]1)[CH2:6][CH2:7][CH3:8])=[O:4].B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[F:1][C:2]([F:21])([F:22])[C:3]([N:5]([CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=2)[CH2:10]1)[CH2:6][CH2:7][CH3:8])=[O:4]

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 225606792,2,2-trifluoro-N-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide

Product 1

HCID 225606602,2,2-trifluoro-N-(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamideYield 94.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of 2,2,2-trifluoro-N-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide (3.4 g, 10.9 mmol) and tetrabutylammonium iodide (4.43 g, 12.0 mmol) in dichloromethane (200 mL) under an inert atmosphere boron trichloride (1 M, 27.2 mL) was added dropwise. The reaction was warmed to room temperature and stirred for 2.5 h. The reaction was quenched by the slow addition of water. The organic layer was separated and dried (MgSO4). This was concentrated onto silica (15 g) and placed on top of a flash column. Chromatography eluting with 30% acetone in hexanes afforded 2,2,2-trifluoro-N-(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide as a foam (3.1 g).

Workup

  1. customThe reaction was quenched by the slow addition of water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationThis was concentrated onto silica (15 g)
  5. washChromatography eluting with 30% acetone in hexanes

Sources & evidence

ORD record
ord-be972d537b8f4704b4f5f4e5bcfc4d7c
Source dataset
uspto-grants-2003_09
Patent number
US06627644B2

Reaction notes

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