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

HRID 1296094ノート

反応式

HRID 1296094 の反応式
[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]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 82050Lithium BromideHCID 35802626-Iodochroman-4-oneHCID 178418348HCID 178418348、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-50d08f3e7a9643a9bc862783daf38150
出典データセット
uspto-grants-2007_07
特許番号
US07244725B2

反応ノート

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