6-Bromo-2-tetralone → HCID 57276089, compound

HRID 1873114Notes

Reaction equation

HRID 1873114 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[O:12])[CH2:6][CH2:5]2.C[Si](C)(C)[O:15][C:16](O)(O)[CH2:17][CH2:18]O[Si](C)(C)C>C(Cl)Cl>[CH2:16]1[O:15][C:7]2([CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[CH2:8]2)[O:12][CH:17]1[CH3:18]

Participants

4

Reactant 2

HCID 27335536-Bromo-2-tetraloneHCID 53644811HCID 53644811, compound

Product 1

HCID 57276089HCID 57276089, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The ketone group of the tetralone is first protected as a ketal. Preferably, ketalization is afforded by slowly adding 1,3-bis-trimethylsilyloxy propandiol to a solution of trifluromethanesulfonate in methylene chloride. Temperatures from about -70° C. to about -60° C. are employed using standard cooling procedures. For example, 6-bromo-2-tetralone is slowly added to a solution of 1,3-bis-trimethylsilyloxy propandiol and trifluromethanesulfonate in methylene chloride to yield 6-bromo-2-tetralone propylene ketal.

Workup

  1. temperatureTemperatures from about -70° C. to about -60° C. are employed using standard cooling procedures

Sources & evidence

ORD record
ord-4eecc7b21fa248a7a21d50123caa1354
Source dataset
uspto-grants-2000_08
Patent number
US06111110

Reaction notes

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