Water → 4-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid

HRID 428214Notes

Reaction equation

HRID 428214 reaction equation
B(F)(F)F.CCOCC.C([SiH](CC)CC)C.O[CH:18]([C:30]1[CH:39]=[CH:38][C:37]2[C:36]([CH3:41])([CH3:40])[CH2:35][CH2:34][C:33]([CH3:43])([CH3:42])[C:32]=2[CH:31]=1)[C:19]#[C:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.O>ClCCl>[CH3:40][C:36]1([CH3:41])[CH2:35][CH2:34][C:33]([CH3:42])([CH3:43])[C:32]2[CH:31]=[C:30]([CH2:18][C:19]#[C:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)[CH:39]=[CH:38][C:37]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 152858234-(3-Hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid

Product 1

HCID 153890694-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.1 ml (8.1 mmol) of BF3.Et2O (48%) and 50 ml of dichloromethane are introduced into a three-necked flask under a stream of nitrogen. 2.6 ml (16.2 mmol) of triethylsilane are added at −20° C., followed by a solution of 1 g (2.7 mmol) of 4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid in 30 ml of dichloromethane and the mixture is stirred at room temperature for 30 minutes. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified on a column of silica eluted with dichloromethane. After evaporation of the solvents, 780 mg (82%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid are collected, with a melting point of 167-8° C.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified on a column of silica
  7. washeluted with dichloromethane
  8. customAfter evaporation of the solvents, 780 mg (82%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid
  9. customare collected, with a melting point of 167-8° C.

Sources & evidence

ORD record
ord-5fa88dfb81d8452b882b943430a7fc5d
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

Loading…