Oxalyl chloride → HCID 59152683, compound

HRID 1804775Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[CH2:13][C:12](=[O:14])[C:5]2[C:6]([C:9](O)=[O:10])=[CH:7][O:8][C:4]=2[CH2:3]1.C(Cl)(=O)C(Cl)=O.[BH4-].[Na+].C([O-])(O)=O.[Na+]>ClCCl.CN(C=O)C.C(OCC)(=O)C.C(O)(=O)C>[CH3:1][C:2]1([CH3:15])[CH2:13][C:12](=[O:14])[C:5]2[C:6]([CH2:9][OH:10])=[CH:7][O:8][C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 12.5 °C

Procedure

6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro-benzofuran-3-carboxylic acid (17) (1 g, 4.8 mmol) is dissolved in 80 ml dichloromethane and after addition of 187 μl DMF (2.4 mmol) the mixture is cooled to 10-15° C. Oxalylchloride (619 ul, 7.2 mmol) is added drop wise and the mixture is stirred for 30 min at room temperature. The mixture is evaporated under reduced pressure, dissolved in THF and cooled to −55° C. A solution of NaBH4 (1.3 g, 34.1 mmol) in 10 ml of DMF is added via syringe. The white suspension is allowed to stir for another 1.5 h at −55° C. 4 ml of acetic acid is added at this temperature and the mixture is poured into 150 ml of a 5% aqueous NaHCO3 solution. The mixture is diluted with ethyl acetate and washed with brine. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (4:6), silicagel).

Workup

customThe mixture is evaporated under reduced pressure
dissolutiondissolved in THF
temperaturecooled to −55° C
stirringto stir for another 1.5 h at −55° C
washwashed with brine
customThe crude product is purified by Flash-chromatography (ethyl acetate/hexanes (4:6), silicagel)

Sources & evidence

ORD record: ord-a53efc95ed73443b845442a7dfc82233
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354431B2

Reaction notes

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