Methanol → 5,11-Bis{[tert-butyl(dimethyl)silyl]oxy}-1,8-dihydro-2H-[1]benzopyrano[4,3-d][1]benzoxepin-8-ol

HRID 2055047Notes

Reaction equation

HRID 2055047 reaction equation
[C:1]([Si:5]([CH3:36])([CH3:35])[O:6][C:7]1[CH:34]=[CH:33][C:10]2[C:11]3[C:20](=[O:21])[O:19][C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH:17]=4)[C:12]=3[CH2:30][CH2:31][O:32][C:9]=2[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CC(C[Al]CC(C)C)C.CO>C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]([Si:5]([CH3:35])([CH3:36])[O:6][C:7]1[CH:34]=[CH:33][C:10]2[C:11]3[CH:20]([OH:21])[O:19][C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:22][Si:23]([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25])[CH:17]=4)[C:12]=3[CH2:30][CH2:31][O:32][C:9]=2[CH:8]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 16682954DibahHCID 210519955,11-Bis{[tert-butyl(dimethyl)silyl]oxy}-1,2-dihydro-8H-[1]benzopyrano[4,3-d][1]benzoxepin-8-one

Product 1

HCID 210519845,11-Bis{[tert-butyl(dimethyl)silyl]oxy}-1,8-dihydro-2H-[1]benzopyrano[4,3-d][1]benzoxepin-8-ol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2,8-Bis-(tert-butyl-dimethyl-silyloxy)-11,12-dihydro-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-one (35 mg, 0.066 mmol) was dissolved in toluene (5 mL) and the resulting solution was cooled to −78° C. A solution of Dibal-H solution (70 μL, 1.5 M solution in toluene) was then added to above reaction mix at −78° C. The reaction mixture was stirred at −78° C. for 3 h. To the reaction mixture was then added methanol (0.5 mL), and then Rochelle solution (2 ml, 1M solution). The reaction mixture was gradually warmed to room temperature. The reaction mix was diluted with CH2Cl2 (30 mL), the organic layer was separated and dried over Na2SO4. The solution was filtered and evaporated to yield a crude product that was purified on SiO2 to yield the title compound as a solid.

Workup

  1. additionmix at −78° C
  2. temperatureThe reaction mixture was gradually warmed to room temperature
  3. additionThe reaction mix
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. customevaporated
  8. customto yield a crude product that
  9. customwas purified on SiO2

Sources & evidence

ORD record
ord-ff6d80b243dc4803bd41bc2310269527
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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