(R)-chroman-2-carboxylic acid → (2R)-6-Iodochromane-2-carboxylic acid

HRID 47664

反応式

HRID 47664 の反応式
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C@@H:2]1[C:11]([OH:13])=[O:12].[I:14](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(O)(=O)C.O.[Cl-].[Zn+2].[Cl-]>[I:14][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[O:1][C@@H:2]([C:11]([OH:13])=[O:12])[CH2:3][CH2:4]2

参加物

6

反応物 2

HCID 6933107(R)-chroman-2-carboxylic acidHCID 56924451Trimethylbenzylammonium Dichloroiodate

生成物 1

HCID 9966213(2R)-6-Iodochromane-2-carboxylic acid

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

(2R)-3,4-Dihydro-2H-chromene-2-carboxylic acid (WO 99/32476) (26.7 g, 150 mmol), benzyltrimethyl-ammonium dichloroiodate (50.1 g, 144 mmol) and zinc chloride (25.3 g, 186 mmol) were stirred in glacial acetic acid (500 mL) under argon at room temperature for 18 hours. The solid was removed by vacuum filtration and then washed with acetic acid (100 mL). The filtrate was concentrated in vacuo to obtain a solid which was slurried in water (300 mL). The crude product was obtained as a pink solid after vacuum filtration and dried (38.3 g, 84%): 1H NMR (DMSO-d6) δ1.95-2.10 (m, 1H), 2.60 (m, 1H), 2.70-2.80 (m, 1H), 4.79 (dd, J=6.0, 3.9 Hz, 1H), 6.63 (d, J=8.4 Hz, 1H), 7.36 (dd, J=8.1, 1.8 Hz, 1H), 7.38 (d, J=1.8 Hz, 1H). CI-MS m/z 305 (M+H+). The crude was used for next step directly.

後処理

  1. customThe solid was removed by vacuum filtration
  2. washwashed with acetic acid (100 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto obtain a solid which

出典と根拠

ORDレコード
ord-d16328e053c74801a885733829e85f4e
出典データセット
uspto-grants-2004_03
特許番号
US06699860B2

関連ノート

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