Sulfuric Acid → HCID 68855467, compound

HRID 1986999Notes

Reaction equation

HRID 1986999 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]3[O:10][C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1.CC(C[AlH]CC(C)C)C.S(=O)(=O)(O)O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]3[O:10][CH:9]2[OH:17])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14487Diisobutylaluminum hydrideHCID 68852565HCID 68852565, compound

Product 1

HCID 68855467HCID 68855467, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-(3-chlorophenyl)hexahydro-1-benzofuran-2(3H)-one (540 mg, 2.19 mmol) in dry tetrahydrofuran (7 mL) was cooled to −78° C. under nitrogen and was treated dropwise with a solution of DiBAL (1.0 M in toluene, 3.07 mL, 3.07 mmol). The resulting solution was stirred at −78° C. for 2 h, after which time the reaction was treated a 1 M aqueous solution of sulfuric acid to dissolve precipitated salts. The reaction mixture was allowed to warm to room temperature and was partitioned between diethyl ether and water. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and brine and was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified via Biotage Horizon (FLASH 25 M, silica, gradient from 0% EtOAc/hexane to 35% EtOAc/hexane) to yield 0.38 g (69%) the lactol, 3-(3-chlorophenyl)octahydro-1-benzofuran-2-ol as a white foam. HRMS: calcd for C14H17ClO2−H, 251.0817; found (ESI, [M−H]−), 251.0835.

Workup

  1. dissolutionto dissolve
  2. customprecipitated salts
  3. temperatureto warm to room temperature
  4. customwas partitioned between diethyl ether and water
  5. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and brine
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified via Biotage Horizon (FLASH 25 M, silica, gradient from 0% EtOAc/hexane to 35% EtOAc/hexane)

Sources & evidence

ORD record
ord-8553549d972445e9b11918bd1843a5e0
Source dataset
uspto-grants-2009_06
Patent number
US07550456B2

Reaction notes

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