Acetone cardice → (2-Ethyl-benzofuran-3-yl)-(2'-hydroxy-[1,1';3',1"]terphenyl-5'-yl)-methanone

HRID 1067320Notes

Reaction equation

HRID 1067320 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:33]=[CH:32][CH:31]=[CH:30][C:6]=2[C:7]=1[C:8]([C:10]1[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]([O:22]C)=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=1)=[O:9])[CH3:2].B(Br)(Br)Br.C(Cl)Cl.C(=O)=O.CC(C)=O>C(Cl)Cl>[CH2:1]([C:3]1[O:4][C:5]2[CH:33]=[CH:32][CH:31]=[CH:30][C:6]=2[C:7]=1[C:8]([C:10]1[CH:15]=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:13]([OH:22])=[C:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:11]=1)=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 18522661Acetone cardiceHCID 22277759Boron tribromide dichloromethaneHCID 23445613(2-Ethyl-benzofuran-3-yl)-(2'-methoxy-[1,1';3',1"]terphenyl-5'-yl)-methanone

Product 1

HCID 23445634(2-Ethyl-benzofuran-3-yl)-(2'-hydroxy-[1,1';3',1"]terphenyl-5'-yl)-methanoneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −78° C., to a stirred solution of (2-ethyl-benzofuran-3-yl)-(2′-methoxy-[1,1′;3′,1″]terphenyl-5′-yl)-methanone (1.07 g, 2.47 mmol) in CH2Cl2 (10.1 mL) was added dropwise 1M boron tribromide/ CH2Cl2 (5.2 mL). After the addition was complete, the dry ice/acetone bath was replaced with an ice water bath and the reaction was stirred for 72 h, eventually warming to ambient temperature. The reaction was carefully quenched with crushed ice, diluted with H2O (16 mL) and extracted with ether. The ethereal extracts were dried (MgSO4) and concentrated. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 0.86 g, (83%) of the title compound as a white solid, mp 142-143° C. 1H NMR (DMSO-d6) δ1.24 (t, 3H), 2.90 (quartet, 2H), 7.28-7.66 (m, 16H), 9.37 (s, 1H). IR (KBr) 3200, 2950, 1625, 1560 and 1175 cm−1. mass spectrum (EI), m/z 418 (M+). Anal. Calcd. for C29H22O3.0.35H2O: C, 82.00; H, 5.39; N, 0.00. Found: C, 82.06; H, 5.40; N, 0.07.

Workup

  1. additionAfter the addition
  2. customThe reaction was carefully quenched with crushed ice
  3. additiondiluted with H2O (16 mL)
  4. extractionextracted with ether
  5. dry with materialThe ethereal extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customPurification on Biotage KP-Sil
  8. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-9c481e601e6244e1a58a23f3cdf345b4
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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