Boron Trichloride → HCID 135814979, compound

HRID 2216511Notes

Reaction equation

HRID 2216511 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[N:18]=[C:17](/[CH:26]=[CH:27]/[C:28]([O:30][CH3:31])=[O:29])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[CH:20]1([N:19]2[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[CH:16][C:17](/[CH:26]=[CH:27]/[C:28]([O:30][CH3:31])=[O:29])=[N:18]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 11384502HCID 11384502, compound

Product 1

HCID 135814979HCID 135814979, compoundYield 122.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ester 2.3 (50 mg, 0.120 mmol) in CH2Cl2 (2 ml) at −50° C. was added a 1M solution of BCl3 in CH2Cl2 (600 μl 0.60 mmol), and the mixture was stirred for 30 min at that temperature before being quenched with MeOH, diluted with EtOAc, washed with H2O, saturated NaHCO3 (2×), brine, and dried (Na2SO4). After concentration, the residue was combined with another 0.024 mmol batch for purification by SiO2 chromatography (30% EtOAc/hexanes) to afford 48 mg (100%) of phenol 3.1. MS (ESI) 327.3 (MH+), 325.3 (MH−).

Workup

  1. custombefore being quenched with MeOH
  2. additiondiluted with EtOAc
  3. washwashed with H2O, saturated NaHCO3 (2×), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentration
  6. customthe residue was combined with another 0.024 mmol batch for purification by SiO2 chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fba7d3fda33448999954c59dcb781e94
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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