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

HRID 47664

반응식

HRID 47664 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-d16328e053c74801a885733829e85f4e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699860B2

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