Ammonium Chloride → 6-Iodo-4-methylchroman-4-ol

HRID 1296094노트

반응식

HRID 1296094 반응식
[Li][CH3:2].[Li+].[Br-].[I:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2=[O:16].[NH4+].[Cl-]>O.C1COCC1>[I:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2([CH3:2])[OH:16]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 82050Lithium BromideHCID 35802626-Iodochroman-4-oneHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 602068356-Iodo-4-methylchroman-4-ol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

CeCl3 (4.9 g, 19.8 mmol) was dried in vacuo at 140° C. for 3 h and then slurried with dry THF (100 ml) for 1 h. The white suspension was chilled to −78° C. followed by the addition of MeLi.LiBr (14.2 ml, 21.4 mmol) over 15 minutes. The mixture was stirred for 30 min followed by the addition of a THF (20 ml) solution of 6-iodo-2,3-dihydro-4H-chromen-4-one dropwise via syringe. After 30 min TLC (15% EtOAc/hexanes) indicated complete reaction. The mixture was treated with NH4Cl (aq.) 30 ml and diluted with water 150 ml. The mixture was extracted with EtOAc and the organic layer dried over Na2SO4. The Na2SO4 was removed by filtration and the filtrate concentrated in vacuo to yield 6-iodo-4-methylchroman-4-ol as an off white solid 4.7 g (95%). HRMS (ESI+) calcd for C10H11IO2 m/z 289.9806 (M+H)+. Found 289.9803.

후처리

  1. customreaction
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe organic layer dried over Na2SO4
  4. customThe Na2SO4 was removed by filtration
  5. concentrationthe filtrate concentrated in vacuo

출처 및 근거

ORD 기록
ord-50d08f3e7a9643a9bc862783daf38150
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244725B2

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