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Triethylamine → 4-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

HRID 1859586
ノート
印刷プレビュー

反応式

HRID 1859586 の反応式
[OH:1][C:2]1[CH2:7][C:6]([CH:15]([CH3:17])[CH3:16])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:5][C:4](=[O:18])[CH:3]=1.C([SiH2][O:24][C:25](C)(C)[C:26]1[S:30][C:29]([CH:31]([CH3:33])[CH3:32])=[C:28]([S:34]S(C2C=CC(C)=CC=2)(=O)=O)[CH:27]=1)(C)(C)C.CCN(CC)CC.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.C1COCC1.C(#N)C>[OH:1][C:2]1[CH2:7][C:6]([CH:15]([CH3:16])[CH3:17])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:5][C:4](=[O:18])[C:3]=1[S:34][C:28]1[CH:27]=[C:26]([CH2:25][OH:24])[S:30][C:29]=1[CH:31]([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

8

反応物 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 546770164-Hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-oneHCID 131723784HCID 131723784、化合物

生成物 1

HCID 546770324-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The title compound was prepared according to General Method 16b using 4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (Example E-20; 0.200 g, 0.75 mmol), toluene-4-thiosulfonic acid S-[5-(tert-butyl-dimethyl-silanyloxymethyl)-2-isopropyl-thiophen-3-yl]ester (Example BB-9; 0.377 g, 0.83 mmol), NEt3 (0.209 mL, 1.50 mmol), and acetonitrile (1.5 mL). As part of the purification, the silylether was cleaved by dissolving the crude coupled product in THF (50 mL) and then treated with a 1.0 M THF solution of tetrabutylammoniumflouride (1.5 mL, 1.5 mmol). After 30 minutes, the mixture was diluted with H2O and extracted with EtOAc. The organic layers were then combined, dried (MgSO4), and concentrated. The resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2) to provide the title compound, mp 52-54° C.

後処理

  1. customThe title compound was prepared
  2. customAs part of the purification
  3. dissolutionby dissolving the crude
  4. extractionextracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washThe resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-e24597c0faff4a2dbb0e03a22d77d4c1
出典データセット
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06528510B1

反応ノート

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