Hydrochloric Acid → [7-(Methylsulfonyl)-3,4-dihydro-2H-chromen-2-YL]methanol

HRID 39032Notes

Reaction equation

HRID 39032 reaction equation
[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([C:15](OCC)=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Li+].[BH4-].C1COCC1.Cl>CCOC(C)=O>[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([CH2:15][OH:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 66879141Ethyl 7-(methylsulfonyl)chromane-2-carboxylate

Product 1

HCID 66878595[7-(Methylsulfonyl)-3,4-dihydro-2H-chromen-2-YL]methanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 7-(methylsulfonyl)chromane-2-carboxylate (0.6 g, 2.1 mmol), LiBH4 (0.18 g, 8.5 mmol) and THF (8 ml) was stirred at 0° C. for 15 min and 2 h at room temperature. HCl (10%) and EtOAc was added, the organic phase was dried (Na2SO4), filtered and concentrated to give the title compound. Yield 0.66 g. MS m/z (rel. intensity, 70 eV) 507 (20), 485 (25), 265 (23), 244 (13), 243 (M+1, bp).

Workup

  1. dry with materialthe organic phase was dried (Na2SO4)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3a584eaecbf348fa818d3175309be6d8
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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