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Ammonium Chloride → 1-(2-Chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanol

HRID 916047
ノート
印刷プレビュー

反応式

HRID 916047 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH3:10].[Li+].CC([N-]C(C)C)C.[O:19]1[C:23]2[C:24]([C:28]([CH3:33])([CH3:32])[CH2:29][CH:30]=[O:31])=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][CH2:20]1.[Cl-].[NH4+]>C1COCC1.CN1C(=O)N(C)CCC1.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH:30]([OH:31])[CH2:29][C:28]([C:24]1[C:23]2[O:19][CH2:20][CH2:21][C:22]=2[CH:27]=[CH:26][CH:25]=1)([CH3:33])[CH3:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 888943-Chloro-p-toluonitrileHCID 2724682Lithium diisopropylamideHCID 589599393-(2,3-Dihydrobenzofur-7-yl)-3-methylbutanal

生成物 1

HCID 589600171-(2-Chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanol収率 66%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 22565281tetrahydrofuran 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone溶媒

実験手順

A solution of 2-chloro-4-cyanotoluene (606 mg) in THF/DMPU (1:1, 8 mL) was treated dropwise with LDA (1.8 M in heptane/ethylbenzene/THF, 2.44 mL) at −78° C. After 30 minutes, 3-(2,3-dihydrobenzofur-7-yl)-3-methylbutanal (400 mg) was added in THF (1 mL) and the mixture was subsequently warmed to room temperature. After 1 hour, 5 mL of saturated ammonium chloride solution was added. The organic phase was separated and the aqueous layer was extracted with 20 mL of ethyl acetate. The combined organic phases were washed with three 10 mL portions of water and dried over magnesium sulfate. The solvent was removed. Flash chromatography (hexanes-EtOAc (gradient from 10:1 to 5:1)) of the residue yielded 460 mg (66%) of 1-(2-chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanol as a colorless oil.

後処理

  1. waitAfter 1 hour
  2. customThe organic phase was separated
  3. extractionthe aqueous layer was extracted with 20 mL of ethyl acetate
  4. washThe combined organic phases were washed with three 10 mL portions of water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed

出典と根拠

ORDレコード
ord-a21f9c193894482aaa117c6a31fdbcdb
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07268152B2

反応ノート

読み込み中…

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