4-Hydroxybiphenyl → (2S)-2-(Biphenyl-4-yloxy)-3-methylbutyric acid, methyl ester

HRID 379972ノート

反応式

HRID 379972 の反応式
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][C@H:33]([CH:38]([CH3:40])[CH3:39])[C:34]([O:36][CH3:37])=[O:35].[C:41]1([C:47]2[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1>[C:41]1([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:46]=[CH:45][C:44]([O:32][C@@H:33]([CH:38]([CH3:40])[CH3:39])[C:34]([O:36][CH3:37])=[O:35])=[CH:43][CH:42]=1

参加物

6

反応物 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10887945(R)-Methyl 2-hydroxy-3-methylbutanoate

生成物 1

HCID 131722882(2S)-2-(Biphenyl-4-yloxy)-3-methylbutyric acid, methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Diethylazodicarboxylate (11.5 ml) in dry tetrahydrofuran (40 ml) was added dropwise over 30 minutes to a stirred solution of triphenylphosphine (22 g), methyl (R)-2-hydroxy-3-methylbutanoate (11.2 g, J.Am.Chem.Soc., (1990), 112, 21, 7659) and 4-phenylphenol (14.5 g) in dry tetrahydrofuran (120 ml). The resulting solution was stirred at room temperature overnight and was then concentrated under reduced pressure. A mixture of isohexane:ether (9:1) (750 ml) was added to the residue and the mixture stirred at room temperature for 30 minutes. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with isohexane:dichloromethane (1:4) then (1:1) to give the sub-title compound as a solid, which was recrystallised from hexane to give a crystalline solid (7.9 g).

後処理

  1. concentrationwas then concentrated under reduced pressure
  2. additionA mixture of isohexane:ether (9:1) (750 ml)
  3. additionwas added to the residue
  4. stirringthe mixture stirred at room temperature for 30 minutes
  5. filtrationThe solution was filtered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with isohexane:dichloromethane (1:4)

出典と根拠

ORDレコード
ord-ac1e1952bb2c4d59ab92f68bea10a389
出典データセット
uspto-grants-2001_10
特許番号
US06300352B1

反応ノート

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