Water → 4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene-6-carbaldehyde

HRID 402784Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15].[Li]CCCC.CN([CH:25]=[O:26])C.O>O1CCCC1>[CH3:15][C:5]1([CH3:16])[C:4]2[C:9](=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=[C:2]([CH:25]=[O:26])[CH:3]=2)[O:8][CH2:7][CH2:6]1

Participants

Conditions

Temperature: -78 °C

Procedure

6-Bromo-4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene (154 mg, 0.54 mmol) in tetrahydrofuran (5.44 mL) was cooled to −78° C. and n-BuLi (261 μL, 0.65 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 30 minutes, and then DMF (168 μL, 2.17 mmol) was added dropwise. The resulting mixture was allowed to warm to room temperature, and stirred for 30 minutes before water was added. It was then extracted with EtOAc (2×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes to obtain the desired product as a colorless oil.

Workup

temperatureto warm to room temperature
additionwas added
extractionIt was then extracted with EtOAc (2×)
dry with materialthe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude residue was purified by silica gel chromatography
washeluting with 0-10% EtOAc/Hexanes

Sources & evidence

ORD record: ord-1d3fe5d735954dee874792b29cde22b3
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742110B2

Reaction notes

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