Ethyl Acetate → HCID 69888880, compound

HRID 2083909Notes

Reaction equation

HRID 2083909 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2([C:14]([OH:16])=[O:15])[OH:13].CCCCCCC.C(OCC)(=O)C>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[S:8][CH2:7][CH2:6][C@@:5]2([C:14]([OH:16])=[O:15])[OH:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 22731979HCID 22731979, compound

Product 1

HCID 69888880HCID 69888880, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The enantiomers of 6,8-dichloro-4-hydroxychromane-4-yl-carboxylic acid (2.17 g, 7.77 mmol; from step (v) above) were separated using chiral chromatography (Kromasil TBB; heptane: ethyl acetate: formic acid) affording 0.74 g of the faster moving, not wanted S-enantiomer, and 0.72 g (66%) of the slower moving sub-title compound. ee=98.4%

Workup

  1. customaffording 0.74 g of the

Sources & evidence

ORD record
ord-211253072c7246ee8ec386dcc0b1f833
Source dataset
uspto-grants-2004_04
Patent number
US06716834B2

Reaction notes

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