2-Propanethiol → HCID 11558585, compound

HRID 2103021Notes

Reaction equation

HRID 2103021 reaction equation
[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[C:11]2[C:3]=1[CH:4](O)[CH2:5][C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1.[CH3:19][CH:20]([SH:22])[CH3:21].O.C(=O)(O)[O-].[Na+]>O.Cl.C(OCC)(=O)C>[CH:20]([S:22][CH:4]1[C:3]2[C:11](=[C:12]([CH3:17])[C:13]([CH3:16])=[C:14]([OH:15])[C:2]=2[CH3:1])[O:10][C:6]2([CH2:9][CH2:8][CH2:7]2)[CH2:5]1)([CH3:21])[CH3:19]

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 69055305HCID 69055305, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 11558585HCID 11558585, compound

Reagents, catalysts & solvents 2

HCID 21885828Hydrate;hydrochlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol (290 mg) in acetonitrle (2 mL) was added 2-propanethiol (0.5 mL) and concentrated HCl water solution (5 drops). The solution was stirred at room temperature for 7 hours. The solution was neutralized using sodium bicarbonate water solution to pH about 7. Ethyl acetate was added, washed with water and brine. Evaporation and chromatography (silica gel, hexane-ethyl acetate 0 to 4%) gave 140 mg of 4-(isopropylthio)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol

Workup

  1. washwashed with water and brine
  2. customEvaporation and chromatography (silica gel, hexane-ethyl acetate 0 to 4%)

Sources & evidence

ORD record
ord-3ab65e827b784d99ad5969703c77e06f
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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