Potassium Carbonate → (5-(4-Butylphenyl)thiophen-2-yl)methanol

HRID 1675302Notes

Reaction equation

HRID 1675302 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][OH:8])=[CH:4][CH:3]=1.[CH2:9]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12].C([O-])([O-])=O.[K+].[K+]>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>[CH2:9]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[S:6][C:5]([CH2:7][OH:8])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 41008604-Butylphenylboronic acidHCID 11435467(5-bromothien-2-yl)methanol

Product 1

HCID 59300633(5-(4-Butylphenyl)thiophen-2-yl)methanolYield 19%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 60.2 (0.300 g, 1.55 mmol), 4-n-butylbenzeneboronic acid 60.3 (0.553 g, 3.11 mmol), K2CO3 (0.644 g, 4.66 mmol), and Pd(PPh3)4 (0.180 g, 0.16 mmol) in toluene (5 mL) was stirred overnight at 95° C. The mixture was cooled to room temperature, filtered through a pad of silica gel (EtOAc), and concentrated. The crude product was chromatographed on silica gel (0-40% EtOAc/hexane) to afford 60.4 (0.072 g, 19%). 1H NMR (400 MHz, CDCl3) δ 7.49 (d, 2H), 7.18 (d, 2H), 7.13 (d, 1H), 6.97 (d, H), 4.82 (s, 2H), 2.62 (t, 2H), 1.60 (m, 2H), 1.37 (m, 2H), 0.93 (t, 3H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of silica gel (EtOAc)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (0-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-c0a73328a7004f699b0b1a99907cf0b7
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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