Potassium bisulfate → HCID 15158209, compound

HRID 704688Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.CON(C)[C:21](=[O:28])[CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.OS([O-])(=O)=O.[K+]>C1COCC1>[CH:23]1([CH2:22][C:21]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[O:12][CH2:11][CH2:10][O:9]3)=[CH:4][CH:3]=2)=[O:28])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: -75 °C

Procedure

2-(4-Bromophenyl)dioxolane from Example C (7 g, 0.03 mole) was dissolved in 75 mls of THF and cooled to -75° C. under argon. Tert.butyl lithium (29 ml of 1.7M solution in hexane) was added slowly at -76° C. maintaining the temperature such that it never rose above -40° C. After addition was complete, the solution was recooled to -78° C. and 4.2 g, 0.024 moles) of the product of Example B was added in THF. After completion of the addition, the solution was allowed to warm to 0° C., poured into 0.5N KHSO4 and extracted with ethyl acetate. After washing with brine, the extract was dried over Na2SO4. After the solvent was removed, the residue was chromatographed on silica with 10% ethyl acetate/hexane to give 2.8 g of the title compound.

Workup

temperaturemaintaining the temperature such that it never rose above -40° C
additionAfter addition
customwas recooled to -78° C.
additionAfter completion of the addition
temperatureto warm to 0° C.
extractionextracted with ethyl acetate
washAfter washing with brine
dry with materialthe extract was dried over Na2SO4
customAfter the solvent was removed
customthe residue was chromatographed on silica with 10% ethyl acetate/hexane

Sources & evidence

ORD record: ord-ab654e0579f04b7ba4d3fd16b9f73c89
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988707

Reaction notes

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