Sodium Chloride → HCID 10923477, compound

HRID 346026Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH3:21][O:22][C:23]1[CH:32]=[C:31]2[C:26]([CH2:27][CH2:28][CH2:29][C:30]2=[O:33])=[CH:25][CH:24]=1.[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CN(C)P(N(C)C)(N(C)C)=O.[NH4+].[Cl-].[Na+].[Cl-]>O1CCCC1>[CH2:34]([CH:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[C:30]1=[O:33])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a -78° C. solution of lithium diisopropyl amide (from 43.8 ml (0.312 mol) of diisopropyl amine in 280 ml tetrahydrofuran and 119 ml (0.298 mol) of 2.5M n-butyllithium) was slowly added a solution of 50 g (0.285 mol) of 7-methoxy-3,4-dihydro-1(2H)-naphthalenone in 100 ml tetrahydrofuran. The resultant reaction mixture was stirred 10 minutes at -78° C. The cooling bath was charged to a 0° C. ice bath, followed immediately by the rapid addition of 38 ml (0.32 mol) of benzyl bromide. Hexamethylphosphoramide (106 ml, 0.60 mol) was then added and the resultant solution stirred at 25° C. for 2 hours. The reaction was added to saturated NH4Cl and saturated NaCl, dried over MgSO4, and evaporated to an oil, which was purified via column chromatography on 1 Kg of silica gel eluted with 10% ether-hexane to give 20 g (26%) of the title compound as an oil.

Workup

customThe resultant reaction mixture
additionThe cooling bath was charged to a 0° C. ice bath
dry with materialdried over MgSO4
customevaporated to an oil, which
customwas purified via column chromatography on 1 Kg of silica gel
washeluted with 10% ether-hexane

Sources & evidence

ORD record: ord-9b047ced9b564f4b913d8f5daa05b138
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05059609

Reaction notes

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