Tetrahydrofuran → HCID 57801105, compound

HRID 1817683Notes

Reaction equation

HRID 1817683 reaction equation
CON(C)C([C:6]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][C:8]=2[CH:7]=1)=O.Br[CH2:22][CH2:23]CC=C.[Mg].[NH4+].[Cl-].[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[CH:7]1[C:8]2[CH:9]=[CH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH:18]=[CH:19][C:6]=1[C:32](=[O:33])[CH2:31][CH2:30][CH2:34][CH:22]=[CH2:23]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 707041-Pentene, 5-bromo-HCID 5462224MagnesiumHCID 57801018HCID 57801018, compound

Product 1

HCID 57801105HCID 57801105, compound

Procedure

Phenanthrene-2-carboxylic acid methoxy-methyl-amide (1 g) was dissolved in anhydrous THF (30 ml). A grignard prepared from 5-bromopentene (3 g) and magnesium in anhydrous THF (15 ml), as described in example 23, was added and the mixture stirred for 2 h. Saturated NH4Cl was added and the mixture extracted with petrol. The organic phase was dried and evaporated and purified by column chromatography (petrol/ethyl acetate) to give the title compound as a white powder. δC (CDCl3, 62.9 MHz): 23.4, 33.3, 37.9, 115.4, 123.2, 123.3, 125.1, 127.0, 127.4, 127.8, 127.9, 128.8, 129.4, 129.7, 131.5, 133.0, 133.3, 134.8, 138.2 and 200.1

Workup

  1. additionwas added
  2. extractionthe mixture extracted with petrol
  3. customThe organic phase was dried
  4. customevaporated
  5. custompurified by column chromatography (petrol/ethyl acetate)

Sources & evidence

ORD record
ord-a80daf508da547da82169deed634167d
Source dataset
uspto-grants-2009_10
Patent number
US07598289B2

Reaction notes

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