4-Methylbenzenethiol → HCID 58051012, compound

HRID 1482730Notes

Reaction equation

HRID 1482730 reaction equation
[O:1]=[C:2]([C:9]#[CH:10])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[C:11]1([CH3:18])[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[O:1]=[C:2]([CH2:9][CH:10]([S:17][C:14]1[CH:15]=[CH:16][C:11]([CH3:18])=[CH:12][CH:13]=1)[S:17][C:14]1[CH:15]=[CH:16][C:11]([CH3:18])=[CH:12][CH:13]=1)[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 78114-MethylbenzenethiolHCID 19793897HCID 19793897, compound

Product 1

HCID 58051012HCID 58051012, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-oxohept-6-ynoic acid 3 (1.0 g), 4-dimethylaminopyridine (DMAP, 0.87 g) and p-toluenethiol (1.77 g) dissolved in dry dichloromethane (15 mL) was stirred at room temperature for 72 h. The reaction mixture was then diluted with ethyl acetate (40 mL) and the resulting organic phase washed with acidified water (2×15 mL, made from adding 2 ml of 1N HCl to 250 ml of deionised water) and finally saturated brine (1×10 mL). Volatiles were removed under reduced pressure (rotary evaporation) to yield a reddish brown ‘sticky’ residue which was further purified using silica based flash chromatography (Silica gel 100 C18-reversed phase, Fluka cat. No. 60754). A mobile phase consisting of hexane:ethyl acetate (60:40 v:v) was used to elute the product 2, (0.32 g, TLC Rf=0.50 using a mobile phase of hexane:ethyl acetate (25:10 v/v) acidified with acetic acid). 1H NMR (400 MHz, acetone-d6): δ 1.71 (p, 2H), 2.21 (t, 2H), 2.23 (s, 6H), 2.45 (t, 2H), 2.83 (d, 2H), 4.78 (t, 1H), 7.09 (d, 4H), 7.30 (d, 4H).

Workup

  1. washthe resulting organic phase washed with acidified water (2×15 mL, made from adding 2 ml of 1N HCl to 250 ml of deionised water) and finally saturated brine (1×10 mL)
  2. customVolatiles were removed under reduced pressure (rotary evaporation)
  3. customto yield a reddish brown ‘sticky’ residue which
  4. customwas further purified
  5. washto elute the product 2

Sources & evidence

ORD record
ord-600031ffa69146ee9fb1c346f3e78850
Source dataset
uspto-grants-2016_08
Patent number
US09415115B2

Reaction notes

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