Acetate → HCID 22252776, compound

HRID 1278843Notes

Reaction equation

HRID 1278843 reaction equation
C([O-])(=O)C.[Si:5](Cl)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[Br:13][C:14]1[C:15]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34])=[CH:16][C:17]2[C:18]([CH3:27])([CH3:26])[CH2:19][CH2:20][C:21]([CH3:25])([CH3:24])[C:22]=2[CH:23]=1.[H-].[Na+]>C1COCC1.C(OCC)(=O)C.O>[Br:13][C:14]1[C:15]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6])=[CH:16][C:17]2[C:18]([CH3:26])([CH3:27])[CH2:19][CH2:20][C:21]([CH3:24])([CH3:25])[C:22]=2[CH:23]=1

Participants

8

Reactant 4

HCID 175AcetateHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 22252725HCID 22252725, compound

Product 1

HCID 22252776HCID 22252776, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The acetate obtained above is saponified and the resulting hydroxyl group is then protected according to the following procedure: tert-Butyldimethylsilyl chloride (2.64 g) is added to a mixture of 5-(3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)pentan-1-ol (4.3 g, 11.7 mmol) and 80% sodium hydride (422 mg) in THF (20 ml). The mixture is stirred at room temperature for 2 h. The solution is poured into a mixture of water and ethyl acetate. The organic phase is washed twice with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash chromatography on a column of silica.

Workup

  1. washThe organic phase is washed twice with water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  4. customThe product is purified by flash chromatography on a column of silica

Sources & evidence

ORD record
ord-398532e4782146b4ac7e6a96488efac9
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

Loading…