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Sodium Bicarbonate → (S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate

HRID 926174
ノート
印刷プレビュー

反応式

HRID 926174 の反応式
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[O:24]S(C(F)(F)F)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 89681723(S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

生成物 1

HCID 89681728(S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethyl-sulfonyloxy) naphthalen-2-yl)acetate (1.8 g, 3.9 mmol) in THF (18.2 mL) pre-cooled to −10° C. was treated dropwise with tetrabutylammonium fluoride (1M in THF, 7.8 mL, 7.8 mmol). After 1 hour, saturated NaHCO3 was added and the mixture stirred for 20 minutes. Following extraction of the aqueous layer with EtOAc, the combined organics were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification via Yamazen silica gel column chromatography afforded (S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate. LCMS-ESI− (m/z): [M−H]− calcd for C20H25O4: 329.4. found: 329.1.

後処理

  1. extractionextraction of the aqueous layer with EtOAc
  2. washthe combined organics were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via Yamazen silica gel column chromatography

出典と根拠

ORDレコード
ord-0d8f41e7d5454683b9161bdf2d5d3520
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284323B2

反応ノート

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