Water → 6-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene

HRID 716812Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([CH3:16])([CH3:15])[CH2:10][O:11][CH2:12]OC)[CH:4]=1.O>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[CH2:12][O:11][CH2:10][C:9]2([CH3:16])[CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

1-methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzene (Intermediate 40, 300 mg, 1.3375 mmol) was dissolved in DCM (8 mL), the solution was cooled to −78° C. and titanium tetrachloride (37.928 mg, 0.2000 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 2 hours. water (15 mL) was added and the mixture extracted with EtOAc (25 mL). Organics were dried over Na2SO4, filtered and evaporated to afford a crude that was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 90:10 as eluent affording the title compound (350 mg).

Workup

extractionthe mixture extracted with EtOAc (25 mL)
dry with materialOrganics were dried over Na2SO4
filtrationfiltered
customevaporated
customto afford a crude that
customwas purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 90:10 as eluent

Sources & evidence

ORD record: ord-3ee339be03f0471abc4b5728a6abdd50
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193704B2

Reaction notes

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