Hydrochloric Acid → HCID 59852696, compound

HRID 2373465Notes

Reaction equation

HRID 2373465 reaction equation
C([O:3][C:4]([C:6]1[CH:18]=[CH:17][C:9]2[O:10][CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][O:14][C:8]=2[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.O.Cl>C1COCC1.C1(C)C=CC=CC=1>[CH3:15][C:12]1([CH3:16])[CH2:11][O:10][C:9]2[CH:17]=[CH:18][C:6]([CH2:4][OH:3])=[CH:7][C:8]=2[O:14][CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 59852692HCID 59852692, compound

Product 1

HCID 59852696HCID 59852696, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3,3-Dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carboxylic acid ethyl ester (30) (9.00 g) is dissolved in THF (150 ml) and a 1.5 M solution of diisobutylaluminium hydride in toluene (120 ml) is slowly added. The resulting reaction mixture is stirred 1 h at RT, then cooled to −30° C. and H2O (120 ml) is cautiously added. After letting the temperature rise to RT a 20% aq. HCl solution (100 ml) is added. The ether layer is collected, washed with H2O and dried over Na2SO4 and the solvent is evaporated. Flash chromatography (silica gel, hexane/AcOEt 4:1) yields 7.25 g of (3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-methanol (31), MS (ESI) 208.1 (M•)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to −30° C.
  3. customto RT
  4. additionis added
  5. customThe ether layer is collected
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated

Sources & evidence

ORD record
ord-0dfc3bc5f64149609392f0591304fa98
Source dataset
uspto-grants-2008_12
Patent number
US07459480B2

Reaction notes

Loading…