Sodium Bicarbonate → HCID 11070762, compound

HRID 342231Notes

Reaction equation

HRID 342231 reaction equation
[CH2:1]([N:4]([CH3:28])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[C:14]([OH:27])[CH:13]=1)[CH:2]=[CH2:3].[CH:29]([Mg]Cl)=[CH2:30].C(O)(=O)C.O.C(=O)(O)[O-].[Na+]>C1COCC1.CCOCC.C(Cl)Cl>[CH2:1]([N:4]([CH3:28])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)([OH:19])[CH:29]=[CH2:30])=[C:14]([OH:27])[CH:13]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 11144768HCID 11144768, compoundHCID 21899381Acetic acid--water (1/1)HCID 178461836HCID 178461836, compound

Product 1

HCID 11070762HCID 11070762, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

1.0 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-hydroxy-phenyl]-(4-bromo-phenyl)-methanone in 9 ml of THF/ether (1:1) is added dropwise during 45 min. at 0° C. to 4.8 ml (1.7M in THF) vinylmagnesium chloride solution. The reaction solution is warmed to room temperature overnight, treated with 3 ml of acetic acid/water (1:1) and worked-up with saturated sodium bicarbonate solution/methylene chloride. After drying the organic phase is concentrated and purified over silica gel with methylene chloride/methanol (95:5). There is obtained 0.64 g of (RS)-5-[6-(allyl-methyl-amino)-hexyloxy]-2-[1-(4-bromo-phenyl)-1-hydroxy-allyl]-phenol, MS: m/e 474 (M+H+, 1 Br).

Workup

  1. customAfter drying the organic phase
  2. concentrationis concentrated
  3. custompurified over silica gel with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-6f1e680bc6d04d099e73ea0aa0466744
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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