Water → HCID 18357516, compound

HRID 1422155Notes

Reaction equation

HRID 1422155 reaction equation
Br[C:2]1[C:3]2[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=2[O:5][C:6]=1[CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].C([Li])(C)(C)C.CON(C)[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33].O>CCOCC>[CH2:9]([O:8][CH:7]([O:11][CH2:12][CH3:13])[C:6]1[O:5][C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]=2[C:2]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 18357471HCID 18357471, compoundHCID 183575562-fluoro-N-methoxy-N-methylbenzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 18357516HCID 18357516, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3 g of 3-bromo-2-(diethoxymethyl)-benzo[b]furan in 80 ml of dry ether under nitrogen at -100° C was added 17.4 ml of a 1.7 M solution of tert-butyllithium in hexanes. The solution was stirred at the low temperature for 2 h then a solution of 2.76 g of N-methoxy-N-methyl-2-fluorobenzamide in 20 ml of dry ether was added and the solution stirred at the low tempertature for 10 min. The solution was then allowed to slowly warm to 0° C., water was added and the organic layer was separated, washed with water and dried over sodium sulfate and evaporated. Gravity chromatography eluting 0 to 50% toluene in heptane afforded 0.91 g of 2-(diethoxymethyl)-3-(2-fluorobenzoyl)-benzo[b]furan as an oil, 1H-NMR (200 MHz, CDCl3) d 5.76 (CHOEt).

Workup

  1. stirringthe solution stirred at the low tempertature for 10 min
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. washGravity chromatography eluting 0 to 50% toluene in heptane

Sources & evidence

ORD record
ord-14262ebef45c4ceeaef16ad3c33904ee
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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