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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2422228Generated: November 1, 2026

Tributylphosphine → HCID 57541940, compound

https://huagongshe.com/reaction/2422228

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylphosphineHCID 13831—
Reactant1,1'-(Azodicarbonyl)dipiperidineHCID 73042—
ReactantBenzenepropanoic acid, 4-hydroxy-, methyl esterHCID 79706—
Reactant(R)-(-)-1-IndanolHCID 6971243—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductHCID 57541940HCID 5754194067.5%

Reaction Conditions

Temperature-30 °C

Reaction Steps

Methyl 4-hydroxybenzenepropanoate (4.1 g, 22 mmol) was dissolved in tetrahydrofuran (50 mL) and the mixture was stirred at −30° C. (R)-1-Indanol (98% ee) (3.0 g, 22 mmol), 1,1′-(azodicarbonyl)dipiperidine (5.66 g, 22 mmol) and tributylphosphine (5.6 mL, 22 mmol) were added and the mixture was stirred at −30° C. for 23 hrs. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The mixture was concentrated under reduced pressure and the obtained oil was purified by silica gel chromatography (hexane to hexane/ethyl acetate=10:1) to give the title compound (4.4 g, yield 66%) as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07960369B2
Source datasetuspto-grants-2011_06
ORD IDord-77ecfe1a9e0b483f892211abc6e755d5
Source noteuspto-grants-2011_06