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Formaldehyde → 5-(Tert-butyldimethylsilanyloxy)-5-(1-propylcyclobutyl)pent-2-en-1-ol

HRID 2080906
ノート
印刷プレビュー

反応式

HRID 2080906 の反応式
C([Li])(C)(C)C.[C:6]([Si:10]([O:13][CH:14]([C:19]1([CH2:23][CH2:24][CH3:25])[CH2:22][CH2:21][CH2:20]1)[CH2:15][CH:16]=[CH:17]I)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[CH2:26]=[O:27]>CCCCC.C1COCC1>[Si:10]([O:13][CH:14]([C:19]1([CH2:23][CH2:24][CH3:25])[CH2:22][CH2:21][CH2:20]1)[CH2:15][CH:16]=[CH:17][CH2:26][OH:27])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 712FormaldehydeHCID 53961856tert-Butyl-[4-iodo-1-(Propylcyclobutyl)but-3-enyloxy]dimethylsilaneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 671021205-(Tert-butyldimethylsilanyloxy)-5-(1-propylcyclobutyl)pent-2-en-1-ol収率 33%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

tert-Butyllithium (1.32 mL of a 1.7M solution in pentane, 2.25 mmol) was added to a solution of the vinyl iodide 6 (460 mg, 1.25 mmol) in THF (2.2 mL) at −78° C. After 0.5 h paraformaldehyde (50 mg, 1.67 mmol) was added. The reaction was warmed to room temperature and stirred for 16 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 4:1 hex/EtOAc) yielded 103 mg (33%) of the alcohol 7 as a clear, colorless oil.

後処理

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9fcc1211648d4b1a8b348f06d36723d3
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932420B2

反応ノート

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