Trifluoroacetic acid → 3,5-Diisopropyl-2-hydroxymethyl-6-(pent-1-enyl)-2'-benzyloxy-4'-fluoro-1,1'-biphenyl

HRID 324892

反応式

HRID 324892 の反応式
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[C:7]([C:13]([O:15]C)=O)=[C:6]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:5]=1[C:32](OC)=O)([CH3:3])[CH3:2].[Br-].[CH2:37]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:38][CH2:39][CH2:40]C.C(OCC)(=O)C.FC(F)(F)C(O)=O>CC#N>[CH:10]([C:8]1[C:7]([CH2:13][OH:15])=[C:6]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:5]([CH:32]=[CH:37][CH2:38][CH2:39][CH3:40])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:9]=1)([CH3:11])[CH3:12]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 2724565Pentyltriphenylphosphonium bromideHCID 22005024Dimethyl 3,5-diisopropyl-2'-benzyloxy-4'-fluoro-1,1'-biphenyl-2,6-dicarboxylate

生成物 1

HCID 738587363,5-Diisopropyl-2-hydroxymethyl-6-(pent-1-enyl)-2'-benzyloxy-4'-fluoro-1,1'-biphenyl

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

The desired compound was prepared from dimethyl 3,5-diisopropyl-2′-benzyloxy-4′-fluoro-1,1′-biphenyl-2,6-dicarboxylate (Example 246, Step D) by the procedure described in Example 241, Steps F-I (using pentyl triphenylphosphonium bromide in Step H). The pure product obtained was a clear oil (4.73 g, 52% over 4 steps). 1H NMR (300 MHz, CDCl3): δ 0.67-0.78 (m, 3H), 1.09-1.34 (m, 14H), 1.66-1.88 (m, 3H), 3.16-3.46 (m, 2H), 4.29-4.44 (m, 2H), 4.88-5.04 (m, 2H), 5.27-5.41 (m, 1H), 5.94-6.01 (m, 1H), 6.69-6.78 (m, 2H), 7.00-7.06 (m, 3H), 7.22-7.26 (m, 3H), 7.35 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.18, 14.52, 22.89, 23.05, 24.39, 24.64, 24.94, 25.11, 25.38, 29.73, 30.50, 30.66, 31.68, 35.85, 60.78, 71.07, 71.45, 102.25, 102.59, 108.08, 108.37, 122.33, 122.54, 127.11, 127.22, 127.92, 128.11, 128.51, 129.16, 132.70, 132.83, 133.39, 134.06, 135.96, 136.96, 137.29, 137.35, 147.48, 147.63, 147.79, 156.90, 156.93, 163.26 (d, J=246.6 Hz, 1C). FAB-MS: calculated for C31H37O2F 460; found 460 (M+). Anal. calc for C31H37O2F: C, 80.83; H, 8.10. Found: C, 80.91; H, 8.01. Rf=0.34 (9:1 hexanes:ethyl acetate). HPLC: (C-18, A=0.05% aqueous trifluoroacetic acid, B=CH3CN; linear gradient: 80%-100% B over 20 min; 254 nm, 1 mL/min): R.T. 14.8 min (37.7 area %), 15.2 min (56.0 area %); 93.7% purity (cis- and trans-).

後処理

  1. customThe pure product obtained
  2. customR.T
  3. custom14.8 min (37.7 area %), 15.2 min (56.0 area %)

出典と根拠

ORDレコード
ord-733909419e1c4b19802f80fbcc93aa7d
出典データセット
uspto-grants-2001_04
特許番号
US06218431B1

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