Water → HCID 10880940, compound

HRID 2226745Notes

Reaction equation

HRID 2226745 reaction equation
C([Li])CCC.[CH2:6]([OH:10])[CH:7](O)[CH3:8].Cl.[CH:12]1[C:22]2[CH2:21][CH2:20][C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[C:17](=[CH:27][CH2:28]OCCN3CCC[C@@H](C(O)=O)C3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.[OH2:41]>>[OH:41][CH2:8][CH2:7][CH2:6][O:10][CH2:28][CH:27]=[C:17]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:22]=2[CH2:21][CH2:20][C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]1=2

Participants

5

Reactant 4

HCID 962WaterHCID 1030Propylene GlycolHCID 24842608HCID 24842608, compoundHCID 178418339Butyllithium

Product 1

HCID 10880940HCID 10880940, compound

Procedure

A solution of n-butyllithium in hexanes (16.8 ml, 2.5 M) was added dropwise to ice-cooled propylene glycol (25 ml) under an atmosphere of nitrogen. When addition was complete the mixture was stirred at room temperature for 15 minutes. A solution of crude 5-(2-bromoethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (10.1 g, prepared as described in Example 3) was added in one portion and the reaction mixture was stirred at room temperature for 42 h. Water (40 ml) was added and the mixture was extracted with ethyl acetate (3×75 ml). The combined organic extracts were washed with water (15 ml), dried over sodium sulphate and the solvent was evaporated in vacuo. The oily residue was submitted to column chromatography on silica gel (200 g) using a mixture of THF and n-heptane (3:7) as eluent. Collecting the proper fractions afforded 4.2 g of 5-(2-(3-hydroxypropyloxy)ethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as an oil. TLC: rf=0.18 (SiO2 ; THF/n-heptane=3:7 ).

Workup

  1. additionWhen addition
  2. stirringthe reaction mixture was stirred at room temperature for 42 h
  3. extractionthe mixture was extracted with ethyl acetate (3×75 ml)
  4. washThe combined organic extracts were washed with water (15 ml)
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was evaporated in vacuo
  7. additiona mixture of THF and n-heptane (3:7) as eluent
  8. customCollecting the proper fractions

Sources & evidence

ORD record
ord-ae75efae5dd74d11baae681e4054f57b
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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