Benzyl Alcohol → Benzyl oxolan-3-ylcarbamate

HRID 1929241Notes

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-15e83ce7f5e14ed185c355557dffdf8a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE043431E1

Reaction notes

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