Benzyl Alcohol → Benzyl oxolan-3-ylcarbamate

HRID 1929241ノート

反応式

HRID 1929241 の反応式
[O:1]1[CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:16])C=CC=CC=1.[CH2:26]([OH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([N:36]([CH2:39]C)CC)C>O1CCOCC1>[CH2:26]([O:33][C:39]([NH:36][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:16])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 4661317(R)-Tetrahydro-3-furoic acid

生成物 1

HCID 21864525Benzyl oxolan-3-ylcarbamate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

12.36 ml of tetrahydrofuran-3-carboxylic acid and 27.84 ml of diphenylphosphorylazide in 500 ml of dioxane are combined with 41.91 g of benzyl alcohol and 35.81 ml of triethylamine. The reaction mixture is heated to 100° C. for about seven hours. After cooling to ambient temperature, the reaction mixture is evaporated down using the rotary evaporator. The residue is taken up in 500 ml of methylene chloride and washed twice with 100 ml of 1 N sodium hydroxide solution. The organic phase is dried over magnesium sulfate and evaporated down. The crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (3:1 to 1:2) as eluant. Yield: 15.60 g (55% of theory); mass spectrum (ESI−): m/z=220 [M−H]−; Rf value: 0.78 (silica gel, methylene chloride/methanol=9:1).

後処理

  1. temperatureAfter cooling to ambient temperature
  2. customthe reaction mixture is evaporated down
  3. customthe rotary evaporator
  4. washwashed twice with 100 ml of 1 N sodium hydroxide solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated down
  7. customThe crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (3:1 to 1:2) as eluant

出典と根拠

ORDレコード
ord-15e83ce7f5e14ed185c355557dffdf8a
出典データセット
uspto-grants-2012_05
特許番号
USRE043431E1

反応ノート

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