HCID 9916286、化合物 → HCID 23296000、化合物

HRID 1954302ノート

反応式

HRID 1954302 の反応式
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:34]=[C:33]([CH2:35][CH3:36])[C:18]([O:19][S:20]([C:23]5[S:27][CH:26]=[C:25]([C:28]([OH:30])=[O:29])[C:24]=5[O:31]C)(=[O:22])=[O:21])=[C:17]([CH2:37][CH3:38])[CH:16]=4)[C:4]=2[C:3]=1[CH3:39])[CH:12]=[CH:11][CH:10]=[CH:9]3.B(Br)(Br)Br.C(Cl)Cl.C(=O)=O.CC(C)=O>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:16]=[C:17]([CH2:37][CH3:38])[C:18]([O:19][S:20]([C:23]5[S:27][CH:26]=[C:25]([C:28]([OH:30])=[O:29])[C:24]=5[OH:31])(=[O:21])=[O:22])=[C:33]([CH2:35][CH3:36])[CH:34]=4)[C:4]=2[C:3]=1[CH3:39])[CH:12]=[CH:11][CH:10]=[CH:9]3

参加物

5

反応物 3

HCID 9916286HCID 9916286、化合物HCID 18522661Acetone cardiceHCID 22277759Boron tribromide dichloromethane

生成物 1

HCID 23296000HCID 23296000、化合物収率 82.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

At -78° C., to a stirred solution of 5-[4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-diethyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid (0.374 g, 0.644 mmol) in CH2Cl2 (3.74 mL) was added 1M boron tribromide/CH2Cl2 (2.00 mL). After the addition was complete, the dry ice/acetone bath was replaced with an ice water bath and the reaction was stirred for 1.5 h. The reaction was carefully quenched into crushed ice, diluted with H2O and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 40% EtOAc/hexane to give 0.300 g (82%) of the title compound as an off white solid. 1H NMR (DMSO-d6) δ 1.09 (t, 6 H), 1.59 (s, 3 H), 2.41 (s, 3 H), 2.62-2.73 (m, 4 H), 7.16 (s, 2 H), 7.38-7.47 (m, 3 H), 7.98 (d, 1 H), 8.49 (s, 1 H), 8.68 (s, 1 H).

後処理

  1. additionAfter the addition
  2. customThe reaction was carefully quenched
  3. custominto crushed ice
  4. additiondiluted with H2O
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified on Biotage
  9. washKP-Sil eluting with 40% EtOAc/hexane

出典と根拠

ORDレコード
ord-5aa1648208ef4e5e80f9e7a76dfd60a8
出典データセット
uspto-grants-2000_09
特許番号
US06121271

反応ノート

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