Tetrabutylammonium Fluoride → (R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylate

HRID 524363ノート

反応式

HRID 524363 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][CH2:37][C@H:38]1[CH2:42][CH2:41][S:40](=[O:44])(=[O:43])[N:39]1[CH2:45][CH2:46][CH2:47][C:48]1[S:52][C:51]([C:53]([O:55][CH3:56])=[O:54])=[CH:50][CH:49]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CCOC(C)=O>[OH:36][CH2:37][C@H:38]1[CH2:42][CH2:41][S:40](=[O:43])(=[O:44])[N:39]1[CH2:45][CH2:46][CH2:47][C:48]1[S:52][C:51]([C:53]([O:55][CH3:56])=[O:54])=[CH:50][CH:49]=1

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735581HCID 131735581、化合物

生成物 1

HCID 118688790(R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylate収率 73.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Tetrabutylammonium fluoride (1.95 mL of a 1.0M solution in THF, 1.95 mmol) was added to a solution of the silyl ether 9 (751 mg, 1.29 mmol) in THF (3.0 mL). After stirring for 16 h the reaction was diluted with EtOAc and washed with water followed by brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex followed by 40% EtOAc/hex) afforded 317 mg (73%) of alcohol 10.

後処理

  1. washwashed with water
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex followed by 40% EtOAc/hex)

出典と根拠

ORDレコード
ord-b03920a0709545f08aea8467b1d94392
出典データセット
uspto-grants-2016_05
特許番号
US09340534B2

反応ノート

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