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Chlorodiphenylphosphine → HCID 20039974、化合物

HRID 1762904
ノート
印刷プレビュー

反応式

HRID 1762904 の反応式
Br[C:2]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]([O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])=[C:4]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]=1.C([Li])CCC.[C:26]1([P:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)Cl)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[Li+]>O1CCCC1.CCCCCC>[C:17]([C:4]1[CH:3]=[C:2]([P:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])([CH3:20])([CH3:19])[CH3:18]
参加物反応条件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 66180ChlorodiphenylphosphineHCID 433294Lithium ChlorideHCID 10882840(2,6-Di-tert-butyl-4-bromophenoxy)trimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 20039974HCID 20039974、化合物収率 107.3%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A stirred suspension of 20.0 g (56 mmol) of 4-bromo-2,6-di-tert-butylphenoxy(trimethyl)silane in 80 ml of dry tetrahydrofuran at -78° C. is admixed dropwise with 38 ml (56 mmol) of a 1.55M solution of n-butyllithium in hexane. The resulting homogeneous solution is stirred for 1 hour at -78° C. and then 12.36 g (56 mmol) of diphenylchlorophosphine is added dropwise. The reaction mixture is stirred for 24 hours at room temperature, and then the suspension of lithium chloride is removed by filtration. The solvent is removed in vacuo. The residue is dissolved in 250 ml of diethyl ether and extracted (3×250 ml) with water. The organic phase is dried over anhydrous sodium sulfate and evaporated in vacuo to give 27.8 grams of a yellow liquid. The crude product is purified by preparative HPLC (silica gel, 99:1 heptane:ethyl acetate eluent) to give 10.7 grams (41%) of a white solid, m.p. 76°-80° C.

後処理

  1. stirringThe reaction mixture is stirred for 24 hours at room temperature
  2. customis removed by filtration
  3. customThe solvent is removed in vacuo
  4. dissolutionThe residue is dissolved in 250 ml of diethyl ether
  5. extractionextracted (3×250 ml) with water
  6. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-7f7e08b7485648e2823c02130fa42f63
出典データセット
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04835202

反応ノート

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