tert-Butyl mercaptan → HCID 57064143, compound

HRID 364879Notes

Reaction equation

HRID 364879 reaction equation
[CH3:1][C:2]1([CH3:32])[C@@H:4]([CH:5]=[CH:6][C:7](=[O:13])[S:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C@H:3]1[C:14]([O:16][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)[CH3:18])=[O:15].C(S)(C)(C)C>>[CH3:32][C:2]1([CH3:1])[C@@H:4]([CH:5]=[CH:6][C:7](=[O:13])[S:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C@H:3]1[C:14]([O:16][C@@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1)[CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 6387tert-Butyl mercaptanHCID 56984452HCID 56984452, compound

Product 1

HCID 57064143HCID 57064143, compound

Procedure

Using the procedure of Example 19, 3 g of (R) α-(3-phenoxyphenyl)-ethyl (1R,cis) 2,2-dimethyl-3-[(ΔZ)carboxyethenyl]cyclopropane-carboxylate and tert.-butylmercaptan were reacted to obtain after chromatography over silica gel and elution with a 95-5 hexane-ethyl acetate mixture 0.97 g of the Z isomer of (R) α-(3-phenoxyphenyl)ethyl (1R,cis) 2,2-dimethyl-3-[3-oxo-3-tert.-butylthio-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+134°±3.5° (c=0.65% in chloroform) and 1.10 g of the corresponding E isomer with a specific rotation of [α]D20 =+44.5°±1.5° (c=0.85% in chloroform).

Workup

  1. customwere reacted
  2. customto obtain after chromatography
  3. washover silica gel and elution with a 95-5 hexane-ethyl acetate mixture 0.97 g of the Z isomer of (R) α-(3-phenoxyphenyl)ethyl (1R,cis) 2,2-dimethyl-3-[3-oxo-3-tert.-butylthio-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+134°±3.5° (c=0.65% in chloroform) and 1.10 g of the corresponding E isomer with a specific rotation of [α]D20 =+44.5°±1.5° (c=0.85% in chloroform)

Sources & evidence

ORD record
ord-00d82f4cbdfc42d8b55eeb1be2fee6eb
Source dataset
uspto-grants-1986_08
Patent number
US04607026

Reaction notes

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