Ethanol → 2-Acetyl-4-(2-methoxymethoxy-3,5-di-tert-butylphenyl)benzo[b]thiophene

HRID 1394597Notes

Reaction equation

HRID 1394597 reaction equation
[C:1]([C:5]1[C:6]([O:18][CH2:19][O:20][CH3:21])=[C:7](B(O)O)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:22]([C:25]1[S:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:33](I)[C:27]=2[CH:26]=1)(=[O:24])[CH3:23].C(O)C.C([O-])([O-])=O.[Na+].[Na+]>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:22]([C:25]1[S:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:33]([C:7]3[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=3[O:18][CH2:19][O:20][CH3:21])[C:27]=2[CH:26]=1)(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 179527043,5-Di-tert-butyl-2-methoxymethoxy phenylboronic acidHCID 179527062-Acetyl-4-iodo benzo[b]thiophene

Product 1

HCID 596820552-Acetyl-4-(2-methoxymethoxy-3,5-di-tert-butylphenyl)benzo[b]thiopheneYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 620 mg (2.1 mmol) 3,5-di-tert-butyl-2-methoxymethoxy phenylboronic acid, 377 mg (1.24 mmol) of 2-acetyl-4-iodo benzo[b]thiophene, 72 mg (0.105 mmol, 5%) Pd(PPh3)4 6 mL of ethanol, 1.25 mL of Na2CO3 in 8 mL of toluene was heated to reflux for 12 hours. After cooling and work-up, the crude product was purified over a short silica gel plug (eluent: ethyl acetate/hexane: 10/90) to give 368.6 mg (0.868 mmol, yield: 70%) of pure 2-acetyl-4-(2-methoxymethoxy-3,5-di-tert-butylphenyl)benzo[b]thiophene as a clear oil. 1H-NMR (CDCl3), δ: 7.84 (d, J=7.9 Hz, 1H), 7.79 (s, 1H), 7.53 (t, J=7.4 Hz, 1H), 7.46 (d, J=2.6 Hz, 1H), 7.44 (d, J=2.6 Hz, 1H), 7.19 (d, J=2.5 Hz, 1H), 4.47 (d, J=4.5 Hz, 1H), 4.06 (dd, J=14.2, 7.0 Hz, 2H), 2.81 (s, 3H), 2.54 (s, 3H), 2.02 (s, 3H), 1.49 (s, 9H), 1.33 (s, 9H), 1.23 (t, J=7.3 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. temperatureAfter cooling
  4. customthe crude product was purified over a short silica gel plug (eluent: ethyl acetate/hexane: 10/90)

Sources & evidence

ORD record
ord-345d7afea0374a67a2f3250570e1a9a6
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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