Methanethiol → HCID 13557853, compound

HRID 1154061Notes

Reaction equation

HRID 1154061 reaction equation
[CH3:1][C:2]1([CH3:11])[C:4]2([CH2:9][CH2:8][C:7]([CH3:10])=[CH:6][CH2:5]2)[O:3]1.[H-].[Na+].[CH3:14][SH:15].O>CN(C)C(=O)C>[CH3:10][C:7]1[CH2:8][CH2:9][C:4]([C:2]([CH3:11])([S:15][CH3:14])[CH3:1])([OH:3])[CH2:5][CH:6]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 24758Sodium hydrideHCID 1073031-Oxaspiro[2.5]oct-5-ene, 2,2,6-trimethyl-

Product 1

HCID 13557853HCID 13557853, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 15.2 g of 2,2,6-trimethyl-1-oxaspiro(2.5)oct-5-ene in 100 ml of N,N-dimethylacetamide was added 4.4 g of 60% sodium hydride. The mixture was cooled to 5°-10° C. and saturated with methyl mercaptan. Stirring was continued while heating the reaction mixture to 100° C. over a two and one-half hour period. After an additional hour at 100° C., the reaction mixture was poured into water and extracted twice with n-pentane. The combined extracts were washed with water, dried and Claisen-distilled to give 15.8 g of the desired product, b.p. 83°-85° C. (0.2 mm).

Workup

  1. waitAfter an additional hour at 100° C.
  2. extractionextracted twice with n-pentane
  3. washThe combined extracts were washed with water
  4. customdried
  5. distillationClaisen-distilled

Sources & evidence

ORD record
ord-01ffdffa70e8497caccd15600b888917
Source dataset
uspto-grants-1984_12
Patent number
US04487945

Reaction notes

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