Hydrochloric Acid → HCID 53801422, compound

HRID 565150Notes

Reaction equation

HRID 565150 reaction equation
CC1(C)[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=O)[C:15]([OH:17])=[O:16])[CH:5]=CC1=2.[Li][CH2:21][CH2:22][CH2:23][CH3:24].[Br-].[CH2:26](P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].Cl.[CH3:53]S(C)=O>O>[CH3:24][C:23]1([CH3:53])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14](=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:15]([OH:17])=[O:16])[CH:5]=[CH:21][C:22]1=2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 12051800HCID 12051800, compoundHCID 178418339Butyllithium2×HCID 178444209HCID 178444209, compound

Product 1

HCID 53801422HCID 53801422, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g (3.8 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylic acid and 10 ml of DMSO were introduced into a three-necked flask under a nitrogen stream. 2.37 ml of n-BuLi (1.6 M in hexane) were added dropwise and the mixture was stirred at room temperature for 15 minutes. 2 g (4.5 mmol) of n-heptyltriphenylphosphine bromide were then added and 2.85 ml (4.5 mmol) of n-BuLi (1.6 M in hexane) were added dropwise and the mixture was stirred at room temperature for one hour. The reaction medium was poured into water, adjusted to pH 1 with hydrochloric acid, extracted with ethyl ether, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column, eluted with a mixture of ethyl ether and heptane (40/60). 380 mg (28%) of the expected compound were recovered in the form of an oil after evaporation of the solvents.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. extractionextracted with ethyl ether
  3. customthe organic phase decanted off
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a silica column
  8. washeluted with a mixture of ethyl ether and heptane (40/60)
  9. custom380 mg (28%) of the expected compound were recovered in the form of an oil
  10. customafter evaporation of the solvents

Sources & evidence

ORD record
ord-82a93991c4b14a729b37d17c4878406d
Source dataset
uspto-grants-2001_01
Patent number
US06171603B2

Reaction notes

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