Toluene → HCID 69902352, compound

HRID 1008314Notes

Reaction equation

HRID 1008314 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18]Cl)[C:12]([CH2:20][CH3:21])=[CH:11][C:10]=1[C:22]1[CH:26]=[CH:25][S:24][CH:23]=1)C1C=CC=CC=1.[CH2:27]([O:34][C:35]1[C:40](Br)=[CH:39][C:38](CCOCCCCl)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.S1C=CC(B(O)[OH:55])=C1.[C:57](=[O:60])([O-])[O-:58].[Na+].[Na+].[C:63]1([CH3:69])C=CC=CC=1>C(OCC)C.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(O)CC>[OH2:8].[CH2:20]([C:12]1[CH:11]=[C:10]([C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)[C:9]([OH:8])=[CH:14][C:13]=1[O:15][CH2:16][CH2:17][CH2:18][O:55][C:31]1[C:30]([CH2:29][CH2:63][CH3:69])=[C:27]([CH:28]=[CH:33][CH:32]=1)[O:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=1[C:57]([OH:58])=[O:60])[CH3:21]

Participants

9

Reactant 5

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 22666226HCID 22666226, compoundHCID 22666251HCID 22666251, compound

Product 1

HCID 69902352HCID 69902352, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10311-PropanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Preparation of 3-[2-benzyloxy-4-(3-chloropropoxy)-5-ethylphenyl]thiophene. A mixture of 4-(benzyloxy)-5-bromo-2-(3-chloropropoxy)ethylbenzene (1.90 g, 5.30 mmol), 3-thiopheneboronic acid (2.00 g, 15.9 mmol), tetrakis(triphenylphosphine)palladium(0) (312 mg, 0.270 mmol), 2 M aqueous sodium carbonate solution (4 mL), and n-propanol (4 mL) in toluene (16 mL) was refluxed for 4 h. The mixture was cooled to room temperature, diluted with diethyl ether, washed once with water and once with saturated sodium chloride solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 5% ethyl acetate/95% hexane) of the residue provided 1.54 g (80%) of the title product as a white solid: mp 65-67° C. 1H NMR (CDCl3) δ 7.58 (d, J=2.8 Hz, 1H), 7.49 (d, J=5.2 Hz, 1H), 7.45-7.30 (m, 7H), 6.62 (s, 1H), 5.13 (s, 2H), 4.14 (t, J=5.8 Hz, 2H), 3.81 (t, J=6.3 Hz, 2H), 2.66 (q, J=7.5 Hz, 2H), 2.29 (quintet, J=6.0 Hz, 2H), 1.24 (t, J=7.5 Hz, 3H); MS FD m/e 386 (p); IR (CHCl3, cm−1) 2969, 1613, 1501, 1138. Anal. Calcd for C22H23O2ClS: C, 68.29; H, 5.99. Found: C, 68.53; H, 6.00.

Workup

  1. temperaturewas refluxed for 4 h
  2. washwashed once with water and once with saturated sodium chloride solution
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2b59fd37be345c9b92f4bd0ad0a45fe
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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