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Ethanol → [2'-(N-t-Butylsulfamoyl)-5'n-propylbiphenyl-4-yl]methanol

HRID 36267
Notes
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Reaction equation

HRID 36267 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=1B(O)O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1.[OH-].[Na+].CCO>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=1[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 701194-Bromobenzyl alcoholHCID 19939476(2-(N-(tert-Butyl)sulfamoyl)-5-propylphenyl)boronic acid

Product 1

HCID 19939403[2'-(N-t-Butylsulfamoyl)-5'n-propylbiphenyl-4-yl]methanol

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2.80 g (9.36 mmol) of 2-(N-t-butylsulfamoyl)-5-n-propylphenylboronic acid (from Step B) and 4-bromobenzyl alcohol (5.25 g, 3 equiv) in toluene (125 mL) was added 1.25N NaOH (32 mL), EtOH (86 mL) and tetrakis(triphenylphosphine)palladium(0) (325 mg, 3 mol %). The mixture was stirred at 100° C. under N2 for 3 hours. The reaction was concentrated and the residue was extracted with ethyl acetate. The organic solution was washed with 1N NaOH, H2O and brine. Next, the organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. The product was purified by flash chromatography, eluting with 2:1 hexane-EtOAc, to provide the titled compound; Rf =0.42 (1:1 EtOAc-hexane).

Workup

  1. concentrationThe reaction was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic solution was washed with 1N NaOH, H2O and brine
  4. dry with materialNext, the organic phase was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography
  7. washeluting with 2:1 hexane-EtOAc

Sources & evidence

ORD record
ord-347e6008157e4bbaadb2cda22ee0054c
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05411980

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes