Sodium Hydroxide → HCID 59199335, compound

HRID 2089500Notes

Reaction equation

HRID 2089500 reaction equation
[CH3:1][C:2]([CH3:14])([CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=O.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+].[BH4-].[Na+]>>[CH3:14][C:2]1([CH3:1])[CH:3]([OH:5])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:7][CH2:6]1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20991675HCID 20991675, compoundHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 59199335HCID 59199335, compound

Conditions

Temperature
65 °C

Procedure

A mixture of 2,2-dimethyl-3-phenylsulfanyl-propionic acid (290 mg, 1.38 mmol) and Eaton's reagent (7 mL) is stirred for overnight at 65° C. The mixture is poured onto ice and basified by the addition of 1M aqueous NaOH. The mixture is extracted three times with dichloromethane. The combined extracts are dried with Na2SO4, filtered and concentrated. The resulting residue is then dissolved in ethanol (10 mL). The resulting solution is charged with NaBH4 (82.6 mg, 2.18 mmol). The mixture is stirred for 48 hours, quenched with 10% aqueous HCl, and concentrated to dryness. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 1:4) to afford (3,3-dimethyl-thiochroman-4-ol); 1H NMR (400 MHz, CDCl3) δ ppm 0.98 (s, 3 H), 1.21 (s, 3 H), 1.58 (d, J=5.1 Hz, 1 H), 2.50 (d, J=13.4 Hz, 1 H), 3.26 (d, J=12.4 Hz, 1 H), 4.17 (d, J=4.6 Hz, 1 H), 6.99-7.09 (m, 1 H) 7.11-7.20 (m, 2 H), 7.27 (m, 1 H).

Workup

  1. additionThe mixture is poured onto ice
  2. extractionThe mixture is extracted three times with dichloromethane
  3. dry with materialThe combined extracts are dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe resulting residue is then dissolved in ethanol (10 mL)
  7. stirringThe mixture is stirred for 48 hours
  8. customquenched with 10% aqueous HCl
  9. concentrationconcentrated to dryness
  10. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 1:4)

Sources & evidence

ORD record
ord-3a747e05423741648ec39cb77311a3fc
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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