Benzyl Alcohol → Phenylmethyl 4-nitrobenzoate

HRID 1398281

反応式

HRID 1398281 の反応式
[CH3:1][C:2]1[CH:3]=[C:4](P2(=O)CCCC2)[CH:5]=[CH:6][CH:7]=1.[PH3]=O.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1([SiH3])C=CC=CC=1.C(O)C1C=CC=CC=1>>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

参加物

6

反応物 5

HCID 244Benzyl AlcoholHCID 61084-Nitrobenzoic AcidHCID 12752PhenylsilaneHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178425924HCID 178425924、化合物

生成物 1

HCID 84647Phenylmethyl 4-nitrobenzoate収率 792.7%

反応条件

温度
80 °C

実験手順

The reaction is illustrated in FIG. 9. In air, a 1-dram vial equipped with a stir-bar was charged with phosphine oxide 1 (9.7 mg, 10 mol %), 4-nitrobenzoic acid (51.7 μL, 0.5 mmol), and diisopropyl azodicarboxylate (DIAD, 147.5 μL, 0.75 mmol). The vial was then sealed with a septum, and purged with argon. Distilled Toluene (1.5 mL) was added. Reaction was allowed to stir. Phenylsilane (67.8 μL, 0.55 mmol), and benzyl alcohol (51.7 μL, 0.5 mmol) was added. The septum was replaced with a PTFE-lined screw cap under an inert atmosphere, and the reaction was heated at 80° C. for 24 hours. The crude reaction mixture was filtered through a plug of celite, concentrated in vacuo, and purified via flash chromatography yielding the title compound 63%, 81.0 mg. To the best of our knowledge this is the first example of a Mitsunobu reaction catalytic in phosphine.

後処理

  1. customIn air, a 1-dram vial equipped with a stir-bar
  2. customThe vial was then sealed with a septum
  3. custompurged with argon
  4. additionDistilled Toluene (1.5 mL) was added
  5. customReaction
  6. customcap under an inert atmosphere
  7. customThe crude reaction mixture
  8. filtrationwas filtered through a plug of celite
  9. concentrationconcentrated in vacuo
  10. custompurified via flash chromatography

出典と根拠

ORDレコード
ord-454aa69af3a449a89183fd6b6538ff53
出典データセット
uspto-grants-2014_12
特許番号
US08901365B2

関連ノート

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