Water → tert-Butyl 4-formylnaphthalen-1-ylcarbamate

HRID 2069036Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:28]=[O:29])C.O>C1COCC1>[CH:28]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1)=[O:29]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of tert-butyl 4-bromonaphthalen-1-ylcarbamate (29) (3.00 g, 9.31 mmol) in THF (100 mL) at −78° C. under nitrogen was added n-BuLi (1.6M in hexane, 20.4 mL, 32.6 mmol) and the reaction mixture was stirred at −78° C. for 1 hr. Neat DMF (4.50 mL, 58.1 mmol) was added and the reaction mixture was stirred at −78° C. for 1 hr, then warmed to RT and stirred for a further 1 hr. Water (5 mL) was added and the mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was triturated with isohexane to afford the title compound (30) as a beige solid (2.20 g, 87%): m/z 272 (M+H)+ (ES)+.

Workup

stirringthe reaction mixture was stirred at −78° C. for 1 hr
temperaturewarmed to RT
stirringstirred for a further 1 hr
customthe mixture was partitioned between ethyl acetate (100 mL) and water (100 mL)
washThe organic phase was washed with brine
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe residue was triturated with isohexane

Sources & evidence

ORD record: ord-ae4f0e176b054c7d9f64ffb925b7e2ee
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299073B2

Reaction notes

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