Ammonium Chloride → HCID 86749280, compound

HRID 2396654Notes

Reaction equation

[OH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:25])/[CH:14]([CH2:21][CH2:22][CH2:23]Br)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:9]([O:26][CH3:27])[C:8]([CH3:28])=[C:7]2[C:3]=1[C:4](=[O:29])[O:5][CH2:6]2.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH4+].[Cl-]>C1COCC1>[OH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](/[CH:14]2[CH2:21][CH2:22][CH2:23][CH:15]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])\[CH3:25])=[C:9]([O:26][CH3:27])[C:8]([CH3:28])=[C:7]2[C:3]=1[C:4](=[O:29])[O:5][CH2:6]2

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of ethyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-bromopropyl)-4-methylhex-4-enoate (420 mg) was cooled to -78° C. in THF (50 ml), and a 1M solution of sodium bis (trimethylsilyl) amide (1.88 ml) in THF was added slowly. The reaction was stirred for 45 min at -78° C., and then allowed to warm to 0° C. over 15 minutes, at which time 5 ml of 1N NH4Cl) was added. The THF was evaporated, the aqueous layer extracted with ether, the ether layer washed with 1N HCl, brine, and then dried. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (20%-25% ethyl acetate in hexanes) to give ethyl (E) 2-[-3-(4-hydroxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-methylpropenyl]-cyclopentanecarboxylate (235 mg), a compound of Formula I-ZH-A1, as an oil.

Workup

additionwas added
customThe THF was evaporated
extractionthe aqueous layer extracted with ether
washthe ether layer washed with 1N HCl, brine
customdried
customEvaporation of the solvent
customgave an oil, which
customwas chromatographed on silica gel (20%-25% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-c1d073156faf446d952bb599cf4c80db
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05493030

Reaction notes

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