Dichloromethane → HCID 19029808, compound

HRID 2256355Notes

Reaction equation

HRID 2256355 reaction equation
[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][C:20]([C:22]2[C:31]([O:32]C)=[CH:30][C:29]3[C:28]([CH3:35])([CH3:34])[CH2:27][CH2:26][C:25]([CH3:37])([CH3:36])[C:24]=3[CH:23]=2)=[O:21])[CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].ClCCl.B(Cl)(Cl)Cl>C1COCC1>[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][C:20]([C:22]2[C:31]([OH:32])=[CH:30][C:29]3[C:28]([CH3:35])([CH3:34])[CH2:27][CH2:26][C:25]([CH3:37])([CH3:36])[C:24]=3[CH:23]=2)=[O:21])[CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 19029752HCID 19029752, compound

Product 1

HCID 19029808HCID 19029808, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4 g (8 mmol) of benzyl 2-hydroxy-4-(3-methoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoylmethoxy)benzoate and 20 ml of dichloromethane are introduced into a flask. 24 ml (24 mmol) of a solution of boron trichloride in THF (1M) are added dropwise at -78° C. and under a stream of nitrogen and the temperature is allowed to rise to -20° C., then the reaction mixture is poured into ice-water. The mixture is extracted with ethyl ether, and the organic phase is separated, dried over magnesium sulphate and evaporated. The residue obtained in purified by chromatography on a silica column, eluted with a dichloromethane/hexane mixture (50:50). 3.1 g (80%) of the expected ester of melting point 127°-128° C. are obtained.

Workup

  1. customto rise to -20° C.
  2. extractionThe mixture is extracted with ethyl ether
  3. customthe organic phase is separated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customin purified by chromatography on a silica column
  8. washeluted with a dichloromethane/hexane mixture (50:50)

Sources & evidence

ORD record
ord-5f223468f0274b0a8d7603fe3de513c3
Source dataset
uspto-grants-1997_08
Patent number
US05654331

Reaction notes

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