Methylmercaptan sodium → 2-(Methylthio)-1-(1,4-dioxaspiro[4.5]decan-8-yl)ethanol

HRID 2175514Notes

Reaction equation

HRID 2175514 reaction equation
[O:1]1[CH2:3][CH:2]1[CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1.[Na].[CH3:15][SH:16]>C(Cl)Cl.CN1C(=O)CCC1>[CH3:15][S:16][CH2:3][CH:2]([CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1)[OH:1]

Participants

5

Reactant 2

HCID 45051789Methylmercaptan sodiumHCID 585624888-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 585627902-(Methylthio)-1-(1,4-dioxaspiro[4.5]decan-8-yl)ethanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

8-(oxiran-2-yl)-1,4-dioxaspiro[4.5]decane (202 mg, 1.10 mmol), prepared in the previous step, in DCM (20 mL) was dissolved in NMP (20 mL) and methanethiol sodium salt (297 mg, 4.24 mmol) was added. The mixture was stirred, heating to 80° C. under argon overnight and then cooled to ambient temperature and poured onto water. After extraction with ethyl acetate, the organic layers were concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 0-50% ether) to afford the product.

Workup

  1. temperaturecooled to ambient temperature
  2. additionpoured onto water
  3. extractionAfter extraction with ethyl acetate
  4. concentrationthe organic layers were concentrated in vacuo
  5. customthe residue was purified by flash chromatography (silica gel, 0-50% ether)
  6. customto afford the product

Sources & evidence

ORD record
ord-4ddd968f995249ee809ac24176e6d7e3
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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