2-(Pentylsulfanyl)ethan-1-ol → HCID 70447989, compound

HRID 543024Notes

Reaction equation

S([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]1[CH2:30][C:29]2[CH:28]=[C:27]([OH:31])[CH:26]=[CH:25][C:24]=2[C@@H:23]2[C@@H:14]1[C@H:15]1[C@@:19]([CH2:21][CH2:22]2)([CH3:20])[C@@H:18]([OH:32])[CH2:17][CH2:16]1)(C)(=O)=O.[Br-].C[Si](C)(C(C)(C)C)OCCCCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:67]([S:72][CH2:73][CH2:74]O)[CH2:68][CH2:69][CH2:70][CH3:71]>>[CH2:67]([S:72][CH2:73][CH2:74][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]1[CH2:30][C:29]2[CH:28]=[C:27]([OH:31])[CH:26]=[CH:25][C:24]=2[C@@H:23]2[C@@H:14]1[C@H:15]1[C@@:19]([CH2:21][CH2:22]2)([CH3:20])[C@@H:18]([OH:32])[CH2:17][CH2:16]1)[CH2:68][CH2:69][CH2:70][CH3:71]

Participants

Reactant 3

HCID 2568082-(Pentylsulfanyl)ethan-1-ol

HCID 23352185HCID 23352185, compound

HCID 54277887HCID 54277887, compound

Product 1

HCID 70447989HCID 70447989, compound

Procedure

The process described in Example 32 was repeated using 7α-(7-mesyloxyheptyl)oestra-1,3,5(10)-triene-3,17β-diol (obtained as described in Example 41 using initially 6-(dimethyl-t-butylsilyloxy)hexyltriphenylphosphonium bromide) and 2-n-pentylthio-ethanol (obtained from pentanethiol and 2-bromoethanol) as starting materials. There was thus obtained as an oil 7α-[7-(2-n-pentylthioethoxy)heptyl]oestra-1,3,5(10)-triene-3,17β-diol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

customobtained

Sources & evidence

ORD record: ord-88662932e6754d78bd4b327f944f4f9e
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659516

Reaction notes

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