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

HRID 379972노트

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HRID 379972 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ac1e1952bb2c4d59ab92f68bea10a389
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300352B1

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