Potassium Carbonate → HCID 11429180, compound

HRID 2087023Notes

Reaction equation

HRID 2087023 reaction equation
C([O:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[C:6]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:5]=1)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[Si:20]([O:19][C:6]1[CH:5]=[C:4]([OH:3])[CH:9]=[C:8]([Cl:10])[C:7]=1[O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 11429988HCID 11429988, compound

Product 1

HCID 11429180HCID 11429180, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.236 g (2.97 mmol) of 3,4-bis-(t-butyldimethylsilyloxy)-5-chlorophenyl formate in 10 mL of methanol was added 2.05 g (15.0 mmol) of potassium carbonate at 25° C. The solution was stirred for 30 min., diluted with 35 mL of water, and extracted three times with diethyl ether (50 mL each). The combined extracts were washed with brine, dried (MgSO4), and concentrated to give 1.028 g (90% yield) of 3,4-bis-(t-butyldimethylsilyloxy)-5-chlorophenol. 1H NMR (CDCl3) d 6.45 (d, J=2.8 Hz, 1H), 6.31 (d, J=2.8 Hz, 1H), 1.00 (s, 9H, t-Bu), 0.93 (s, 9H, t-Bu), 0.18 (s, 6H, Me), 0.15 (s, 6H, Me); 13C NMR (CDCl3) d 149.7 (s), 148.9 (s), 137.7 (s), 126.9 (s), 109.8 (d), 107.8 (d), 26.3 (q, 3C), 26.2 (q, 3C), −3.6 (q, 2C, Me), −3.4 (q, 2C, Me). Anal. Calcd for C18H33ClO3Si2: C, 55.57; H, 8.55. Found: C, 55.39; H, 8.87.

Workup

  1. extractionextracted three times with diethyl ether (50 mL each)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3dc0457b3b404e36b2652b400e5f7ebc
Source dataset
uspto-grants-2004_04
Patent number
US06727277B1

Reaction notes

Loading…